February 22, 2024

Scaling a Bootstrapped Business in a Crowded Market with Adam Kay

In this episode, Alper Yurder interviews Adam Kay, CRO of Playroll, delving into Adam's transition from a legal career to sales, his reflections on business growth, and the importance of customer satisfaction for a bootstrapped startup.

Meet our guest

Adam Kay, CRO at Playroll

Adam possesses a varied background in sales, management, and entrepreneurship, having played crucial roles in companies such as Paddle. His transition from law to the tech industry underscores his entrepreneurial drive and dedication to customer satisfaction, shaping his impactful career in business leadership.

Key takeaways

  • Choose a career path that aligns with your interests and values, even if it diverges from conventional expectations.
  • Stay adaptable and commit to ongoing learning to thrive in fast-paced industries.
  • Focus on nurturing existing client relationships to drive revenue growth, rather than solely chasing new leads.
  • Practice prudent budgeting and seek innovative solutions, especially in ventures without substantial funding.
  • Maintain authenticity and prioritize building genuine connections with clients to drive sales success.

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Football fan to a business person

Alper Yurder interviews Adam Kay, CRO of Playroll, discussing Adam's upbringing and early career journey. Adam grew up in North London, where he developed a love for football and an early curiosity about business, sparked by seeing football team names on stock market sheets. 

"What intrigued me was that there were football teams on those share prices... What does this all mean? I don't understand how on a daily basis there can be an up or a down against these... That was my trigger into the world of business."

Despite pressure to pursue a conventional career path, including a stint in law, Adam realized he wanted a career that aligned with his passions and values. Adam reflects on his disillusionment with the legal profession, despite its prestige and financial rewards, and his decision to pursue a career that offered more fulfillment. 

“And so I kind of came to this realization that if you're going to be spending the majority of your waking life committed to a career, you might as well be doing something you enjoy, because you never know what's gonna come out at the end of it.”

He shares his journey from law to sales, highlighting the importance of acquiring skills that align with his interests and values. Despite initial skepticism from family and societal norms, Adam embraced the opportunity to work in sales, recognizing its potential for personal and professional growth in a rapidly evolving industry like SaaS.

"I still don't really know what I'm gonna end up doing, but there is a skill that I knew I needed to learn or have exposure to... sales was a skill that I needed to acquire... So I actually found a graduate sales role for a SaaS company."

Sales, growth, and team dynamics

Adam and Alper discuss various aspects of business growth, career progression, and the mindset required for success in sales and leadership roles. They touch upon the stigma associated with sales as a career choice and the changing dynamics of joining the workforce at a younger age. 

Adam reflects on his journey from a legal profession to sales, highlighting the importance of practical skills over traditional education paths.

“Commercial minds, sales people that I have worked with have not gone to university, have gone straight from school to working and are highly successful people, C-level, VP-level, even kind of just AEs who've kind of stayed in an IC role for the rest of their lives and just taking home enormous pay packets, the university has had no bearing on their kind of career outcome there.”

Adam shares insights from his experience at Paddle, a SaaS company, where he navigated through multiple funding rounds and drove significant revenue growth. He discusses the challenges of transitioning the business from a founder-led sales approach to a more scalable model, emphasizing the importance of adaptability, focus on repeatability, and hiring the right talent. 

"It always starts with, 'What is your total addressable market? Who are we targeting? What's your ICP?' So we really focused on that. And the first thing that I really focused on is about repeatability. We grew to that revenue size and through all that funding with 150 people. We were not a big company. We did it very lean. We were always looking at ways to automate things and create efficiencies."

Adam advocates for a culture of continuous learning and growth, where individuals are curious, ambitious, and willing to embrace change. 

"I think for me, it's somebody who's comfortable with change... somebody who is obsessed with growth... People who harass me for books they should read or podcasts they should listen to. That's the type of behavior that for me not only says you thrive in this environment, but you're actually probably a future leader that I need to invest in..."

He acknowledges the blurred boundaries between work and personal development, suggesting that in a startup environment, success often requires a willingness to go above and beyond traditional work-life balance norms. Ultimately, Adam's approach to business growth and leadership revolves around building a team of passionate, adaptable individuals who are committed to achieving collective success.

Sales strategy in a bootstrapped startup

Alper Yurder and Adam discuss the experience of building and scaling a business from scratch, specifically focusing on Adam's bootstrap approach compared to VC-backed ventures.

"70% of our revenue growth this year is expected to come from existing clients, not from new logos. Meaning, actually, we don't have to spend so much on top of funnel logo acquisition if we do really well by our customers... we need to really focus on, well, what do we need to do to really make sure our customers are happy?"

Adam highlights the challenges and pressures of operating without significant funding, emphasizing the need for cautious budgeting and innovative problem-solving. Despite facing stiff competition in a crowded market, Adam emphasizes the importance of prioritizing customer satisfaction over logo acquisition, noting that a significant portion of their revenue growth comes from existing clients. 

"Humans still like to buy from humans... authenticity, integrity, and credibility cannot be replaced by technology... understanding that whole kind of ecosystem, the key really is... humans still like to buy from humans."


Full episode transcript

Alper Yurder: Great, so today in the therapy chair, I have Adam Kay, CRO of Playroll, the global workforce platform and one of the early users of Flowlane, their sales, development and partnerships teams too. Adam is a lawyer by education, but has been spending the last 15 years or so of his career in commercial leadership roles, from running the EMEA and global sales orgs at Converse Social and Shoutlet, to building the global sales organization at Padoll, we all know, and more recently as CRO. I'm sure he'll have many stories to tell us.

We'll talk about his success, the joy, the pain and the journey. Welcome to CS Therapy Adam. How are you feeling today?

Adam Kay: I'm great. Thank you for the very kind and complimentary induction. Great to be here.

Alper Yurder: OK, I'm glad to hear these intros. I try to keep them like when I have people like you, it's like I have to mention everything, but I have to keep it concise. But anything I missed there, you would like to add?

Adam Kay: No, no, I guess in my head it was just worryingly sounding like an obituary more than anything, but thank you, I appreciate it.

Alper Yurder: Oh, yeah, we'll have one of those. Hopefully we get so close that I get to do you a bit true to. OK, let's go into it. So any good therapy starts with childhood and growing up, Adam. And this is a tradition here. We love understanding how you're growing up, your experiences, shape your values, and the person you are today. So can you tell us you're a Londoner? So can you tell us a little bit about that?

Adam Kay: I'm going to go ahead and turn it off. Yeah, absolutely. I mean, I consider my background to be relatively uneventful. I think that's a positive in today's world. I'm very close with my parents and my family. I grew up in North London, just a stone's throw away from what used to be the twin towers at Wembley Stadium that subsequently became the Arch. And of course, football is mad. Everything was football in my life. Football, football, maybe a bit of computer gaming as well. And I think perhaps that was kind of a recurring memory of my childhood, just being out in the garden, kind of kicking a ball against trees, a goal, my sister's, whoever would really try and stand in the way. And actually, perhaps was also my segue of interest into business because I remember waking up in the morning and you know, my father, myself, every breakfast, reading the paper and I'd be working back to front, so the sports section first, and after the sports section was the share prices, which were on a single sheet. What intrigued me were there were football teams on those share prices, such as Manchester United, Aston Villa. And I'm like, this isn't the league table. This is not the results from the weekend. This isn't the fixture list. What are these numbers? What does this all mean? I don't understand how on a daily basis there can be an up or a down against these. Is this a, you know, is this something that we're going to think about in terms of the end position and from there on in, I actually kind of captured me in terms of ownership, how can a company be owned? What is a company? What is a share? How can that change the price? And really that was my trigger into the world of business there.

Alper Yurder: Oh well. How old were you when this was happening?

Adam Kay: I was about nine or 10 years old.

Alper Yurder: So your introduction to capitalism at the age of 9 or 10. Wonderful.

Adam Kay: Introduction to Kassim, my father is an accountant and at the same time into socialism and talks to me all about taxes and how nothing comes for free and how we must give back as well. So yeah, I think it was a very balanced upbringing, but just a natural curiosity, initially kind of stemming from my love of sports and in particular football, but just kind of exploding out from there.

Alper Yurder: Some of my guests have that. The football analogy, did you ever want to be a coach as well?

Adam Kay: In football, no. Well, to talk about it in the past tense is probably still wrong. I still feel that one day a scout will come and spot me. I'm 42 years old and I appreciate it. But I refuse to stop dreaming. So if anyone out there is thinking about going out on their dreams, don't because it may still happen for me and it will certainly happen for you.

Alper Yurder: Oh good, you're still young. Yeah, you still have time. Okay, fine. Maybe this is gonna be your life-changing moment in cell therapy where you get discovered. Excellent.

Adam Kay: For any football scouts out there, I play football almost as well as I talk.

Alper Yurder: Wow, okay. I do have some... It's the straight male child's dream to become a football player and manager and... Okay, I hope it becomes real for you. How many siblings did you say you had? You had sisters?

Adam Kay: I have two sisters and I'm sandwiched right in the middle between them two from an age perspective.

Alper Yurder: Oh, how was that?

Adam Kay: It was great. I mean, you know, I was very two years apart between all of us Story goes I don't really remember it that when my younger sister was Well, my mother was pregnant with my younger sister I was adamant that it was going to be a boy to the so much so to the extent that when my sister Born I refused to accept that she wasn't a boy and the story goes I was I was about three years old she must have been one I one early Saturday morning, I pulled her out of her cot and decided to cut her hair thinking that will make her a boy. So appreciate how kind of unpolitically correct this talking is in today's world, but it was so much simpler then. At least it kind of immortalized the experience and the fact that we were having professional family photographs taken the next day and bless my sister's got this kind of wonderful zigzag haircut. I guess they call it karma though, looking at my hairline now, that must've been some sort of kind of cosmic payback there for me.

Alper Yurder: Makes sense.

Adam Kay: I'm messing with her hair ahead of the professional photos then.

Alper Yurder: Maybe. So I had the CRO, Virif Javier, and he's my friend from, you know, many, many years, 20 years now. And he's had an incredible career, blah, CRO, this, that. And I was saying like, dude, you still have the same hair. How didn't you lose them along the journey? And because most people I believe around me unfortunately end up losing it. So you're not alone in that department, Adam. That's fine.

Adam Kay: I'm not lying and I'm not ashamed. I wear my bald head with pride.

Alper Yurder: There you go. Own it. Excellent. All right. So we already started talking a little bit about the very, very early days of the career. But can you share with us the journey from being that boy and to your first job, your first sales role, maybe?

Adam Kay: Yeah, absolutely. So I guess in between that and my first sales job was actually a career. Well, not a career is probably an overstatement. A stint in law. Um, actually I got to be in the university and I had no idea what I wanted to do. I think like most people, um, you know, unless you go into university saying I'm going to be a vet or a dentist or a doctor, I didn't know. I did a generic course called management.

Alper Yurder: Stinked, yeah.

Adam Kay: Speaking very candidly and vulnerably, I still don't really know what it was about, but I managed to get through it. And I just decided to apply across the board to kind of well-respected jobs, graduate roles across kinds of industry, banking, management, consultancy, accounting law. And I just said, I'll leave it up to fate. Whatever I'm offered first, I will take because I didn't. And thankfully, a very, very large law firm, I still think it must have been a mistake. offered me an interview, which was wonderful and turned out into a job. So I started working at what's called a Magic Circle law firm, one of the largest law firms in the world. There's a firm called Linklaters. So in the city by... I think they were number two at the time. They must've gone down, but yeah.

Alper Yurder: Yeah. Which one was it? Ah, okay, one of the four, right?

Adam Kay: and joined a cohort of trainees. I had to do two more years of study after university to do a law conversion and then my professional legal exams. And then did two years training at Linklaters in six month rotations in different departments. I'd love to say it was the most positive experience of my life, but I really didn't enjoy it. And… I think it was compounded by the fact that people were telling me just how lucky I am to have been there, people doing kind of summer placements as they're growing up and still not getting a job. And, you know, it's, it's like, it's just the deals that I'm working on are in the financial times the next day. And, you know, for a first job being paid an extortionate amount of money with this wonderful trajectory in front of me. And I just didn't get it. I didn't get what the excitement was about.

Alper Yurder: Hmm. So they were like, be grateful, you are ungrateful.

Adam Kay: Be grateful, get your head down, you'll learn to like it. And you know, it's got security and a kind of fortune at the end of it. And you know, of course, again, fast forward 15, 20 years, I appreciate the value of earning well. It is clearly the primary reason we all go to work. And I still believe that every single salesperson is motivated by financial reward amongst other things. But it wasn't enough for me. And I kind of got to the point of the end where I'm like, I don't want to spend the rest of my life doing this. I think I was promptly helped by the fact that the global credit crunch happened around that time as well. And I know that sounds like quite a perverse statement, but I remember seeing my mentors in the firm who are, you know, really pushing themselves for partnership, working very, very hard, long hours, et cetera and ultimately leaving with a cardboard box at the end of it, because that department was cutting back. And so I kind of came to this realization that if you're going to be spending the majority of your waking life committed to a career, you might as well be doing something you enjoy, because you never know what's gonna come out at the end of it. And so I decided actually, as I said, my father was an accountant. He said, go train to be an auditor, go train to be an accountant. I got a job to train again at PWC which was also one of the most respected accounting firms. And I decided to take a little break between the two and thought, well, I don't know what I want to do still. I've no idea what I'm gonna end up doing, but there is a skill that I knew I needed to learn or have exposure to because it's highly true. I was 26 at the time.

Alper Yurder: How old were you by then?

Adam Kay: I was still very young, but I was married, I had a child on the way. So it wasn't just about living off of my parents, I had responsibilities and I had to learn. But I still didn't know where I was going to go.

Alper Yurder: Oh wow. Ah. Okay. You know, I only started working at 26. I only started working at 26. I did my master, I took my time, yeah. So, you know, different.

Adam Kay: Well, I think there's a lot of value in that. Again, if you're able to do so I was, you know, again, if I'd have started four years earlier, which is when I graduated, I'd have been working from 22. But I've been through the law. So I decided to break this more common path. Yeah, and it's the more it's the more I guess, respected path. It's actually quite interesting, I know.

Alper Yurder: Yeah. I think your path is the more common path. Your path is definitely the more common path. Yeah.

Adam Kay: I'm doing a lot of work. We've got a big team out in South Africa at the moment. And its sales in South Africa very much reminds me of sales in the UK, circa 2007, 2006, where it was a dirty word. It wasn't a career that people really thought about. SAS was not a thing yet. Neither were any of the bubbles that came after that. And so, you know, again, when I told my grandmother that I'm leaving a corporate law to become a salesman, you know, she scolded me. She thought, you're going to call me in the evening to sell me insurance. I'll knock on my door to sell me nights. B2B SaaS was just not a sales. Sorry. It was just not a thing. Um, but I wanted to acquire this skill because I knew whatever I ended up doing in law, accountancy, consulting, entrepreneurial sales was a skill that I needed to acquire. So I actually found a graduate sales role for a SaaS company. I thought it was something to do with the armed forces. I didn't know what SaaS was. But it turns out it's not the special airborne service. It is, you know, software as a service. And I believe I was working for one of the first SaaS businesses in the UK, which is a company called Meltwater. Now a very, very large successful public company. And selling media monitoring or online monitoring for PR and communications professionals, reputation management. Yeah

Alper Yurder: All right. I'll, I'll pause you there because before we go into the detail of that, there's like two things which, which I completely agree with. Well, sales being a dirty word, which I always talk about. I made the transition from consultants to sales and all my friends were like, dude, like, what's wrong with you? It's not even respect. Are you just going to be a sales guy? And the second thing about that age thing, and I see a lot of people now, obviously in Flowla, is that we have a lot of Gen Z employees. The people, especially in my marketing team, they're quite young. Some of them aren't doing it as their first job, et cetera. And I think people join the workforce quite younger than they used to, or at least on average, but also in other places in the world that's starting. Like Germany is traditionally like a late bloomer, you do your, you know, travel the world and then go back to work. But a lot of people are feeling the pressure to join work earlier and earlier. Maybe it's a cost of living crisis thing. Side note.

Adam Kay: Yeah. Maybe it's the cost of living. I think again, from my experience and again, university, I thankfully were in a position to be able to afford it. My family, but it was never, it was never a conversation. It was always inevitable. I mean, my grades were good enough. It was, you have to work hard at school so you can get into university and you have to work hard at university so you can get a good job. Like it just wasn't kind of considered to go a different route. I have since, and I'd argue that some of the best

Alper Yurder: just do it.

Adam Kay: Commercial minds, sales people that I have worked with have not gone to university, have gone straight from school to working and are highly successful people, C-level, VP-level, even kind of just AEs who've kind of stayed in an IC role for the rest of their lives and just taking home enormous pay packets, the university has had no bearing on their kind of career outcome there.

Alper Yurder: So what do they have that makes them successful?

Adam Kay: I think kind of commercial instinct and I'm still unsure if this can be taught or if this is innate. Naturally if it's innate. Yeah. I think they have focus and ambition. You know, the opposite of which is entitlement. You know, these are people who want to prove themselves. I guess, you know, they do feel they are less sophisticated, intelligent.

Alper Yurder: Yeah, art or science.

Adam Kay: have achieved less as a result of not going to university and therefore feel they need to prove more. I feel that is a ridiculous statement, but it's easy for me to judge having been to university. But I think it creates this drive for them to prove success. And I think ultimately they are relationship builders, which is what sales always comes back down to. Call me old fashioned, but people buy from people. And so being able to build relationships, authentic relationships and understand the prospect, again, you don't need to go to university to learn how to do that.

Alper Yurder: Yeah, well, I mean, call me psychologically distorted, but I always take the drive from the need to be better with a pinch of salt, of course, over the feeling of entitlement. So I'll take it, I'm one of those. I try to do the work to feel enough and whatever, but you know what? The opposite is much worse. In my lifetime of my career, I've seen people with a feeling of, oh, it's just okay. No, you don't get too far. Of course you need a healthy balance, anybody will say but.

Adam Kay: Of course, but again, it reminds me even as we were talking before this started talking about kind of my journey and giving advice to people on who want to get there, I'm like, get where? I haven't got anywhere. I'm still the same guy who is trying to figure it out. I have a different responsibility and a different job now, but I haven't achieved more than anyone else or I haven't done anything more than anyone else. I'm just this is my role now and every single role, every single day, call it kind of

Alper Yurder: What do you mean you haven't achieved? What do you mean by that? Let's unwrap that. What do you mean? Like you are the CEO of a very successful company. You were in the SaaS very competitive market for 10 years. You were at pedal, the stat. Like what do you mean you haven't achieved?

Adam Kay: Yeah, yeah. When I see it on paper, I'm like, wow, let's take an example. When I, when I stepped off, um, the journey at paddle, which I decided to do in, uh, the summer, late summer of 2022, I'd been there four years fully vested, yada yada, you know, I'd learned my niche and I, you know, if I am successful in a role, I stop enjoying it because I'm successful in growing the company. And I'm an early stage small business. Um, every day seems like.

Alper Yurder: Okay. I'm sorry for you. I'm first of all, I'm sorry for you, but yeah, let's go on. You can't just enjoy the comfortable life of, you know, being in a grown up company. You just have to torture yourself again.

Adam Kay: I don't know why I'm not doing it. I'm not doing it for the punishment. But I think that's part of it, is that every day I want to feel like it's a fresh new challenge and it's an existential one that we may not be here tomorrow. And that's why I constantly feel like we've not achieved or I've not achieved anything. And Paddle particularly, we grew from sub five to north of 80 million in four years, several rounds of funding, huge, huge growth, very exciting. But It never felt like it when we were doing it. Only when I stopped and I looked back and I'm like, wow, what did we achieve? Wow. And it always felt like everything was about to fall apart. And hey, I love that feeling. That's what kind of gives me adrenaline. That's what gives me this kind of drive. But it's also kind of, I think it's quite grounding to say, you haven't done anything. you haven't done anything yet, right? And for me, I don't think that will ever end. It drives me forward. I've learned to balance that with my life and there have been times where that feeling of not achieving anything has overwhelmed me personally and mentally, and I've had to kind of work at that as well to say, it's okay, it's okay to feel like that.

Alper Yurder: Yeah, I mean, interviewing so many CROs now, I don't know how many I've done in the past two years and now with a podcast. A very common thread is that it's so interesting. We look like outsiders to the people who are successful and we think, wow, like they have a choose-for-mine, they're like, you know, this guy, that girl, you know, big, big shots etc. And almost all of them exclusively say during the time it didn't feel that way. You know, when I was going through that journey, it was like, not enough, we have to do more, achieve, achieve. And very few were taking stock of what they are doing and feeling like they were becoming that person who is doing a lot, which is very fascinating to me. I wonder why that is.

Adam Kay: Well, it's less about status and title and bank balance, if I'm being honest. And again, my bank balance does motivate me. It's an ambition of mine. Um, but actually that kind of sense of satisfaction is when I pay for a family holiday, when I'm paying them all, it sounds ridiculous because it's what most people do, um, and naturally people have different kinds of means in terms of, well, how big is their budget for a holiday or the house, whatever it might be. But it's my sense of achievement that I've been able to do this without any support or leveraging any kind of you know family contacts. It's off my own back and a merit that I've been able to do this, not the fact that I've achieved a C-level title. For me the title is you know an SDR is probably more important than I am they have a direct fingerprint on the revenue they generate do I? No I'm not selling I'm not calling people I'm not creating meetings anymore. So for me, my job is to kind of, yes, build the strategy and orchestrate things in the past, but that's my job and I haven't done it yet. So, you know, that's why again, it's, it's an imposter syndrome. Is it just my view of the world? But it's, I always feel like there's a bigger mountain to climb next than anything I've achieved.

Alper Yurder: Okay, I think I have the dose of it that is needed. I'm gonna take a different course now, not a different course, but expand on the business side of things a little bit. So for example, we started talking about the journey at Paddle, which must be fascinating. How many years were there? Four years, did you say? I saw all your shares wasted, I hope. Or pot, okay, good, good. Okay, that's a great place to be. So that was from, what's...

Adam Kay: Peace. Four years. Four years, yeah. Yes they did, thankfully.

Alper Yurder: level of investment to, what was it, series D? Um, that they're in.

Adam Kay: So yeah, I think we've just done Series A after I joined, about six months after I joined. And I know that because that year, the business forgot to run as a business. It ran as a recruitment agency and it was just busy putting people on boards. And I was the last of my team to be hired. It had grown from Harrison, the founder doing the sales to now a team of 30 SDRs, AEs, and solution architects. We had this concept called LDR lead development reps, which was a horrific job, people just kind of putting website domains into, into Excel and considering whether we could sell them or not. Um, and, and trying to, and the business for the first time in the past four years hadn't grown by triple digits and kind of the investors were panicking cause they'd just done a sizable series eight. And the business had kind of, I mean, not plateaued, it's beginning to contract in terms of, you know, net dollar retention particularly. And so I was brought on at the end of that hiring cycle to get back to triple digit growth again.

Alper Yurder: Oh wow, no pressure.

Adam Kay: No pressure. Again, it's what's the I didn't

Alper Yurder: So you were there from A to D. Was that it?

Adam Kay: I was there from A to D, absolutely. There was a B round, C round, a mezzanine round, somewhere in the middle of those two, and a D round, as well as the acquisition of ProfitWell, which happened about six months before I left.

Alper Yurder: Oh my god. Okay. So do you mind telling us a little bit, like maybe let's cover them a little bit because I think what I like with sales therapy is if there's a person who's going from A to B, B to C, C to D in your shoes, in those roles right now, like I'd like them to hear from the man who did it. Like what were the highlights, the lowlights, the challenge, the focus, how did it change? Let's start diving into that a little bit if you don't mind. So from A to B maybe let's start, or you do your own way, give us a general overview, whatever you prefer.

Adam Kay: I think I've lost your output. Sorry dude, I missed the last 10 seconds. I think you just cut it out. So from A to...

Alper Yurder: Oh, no, I was saying, A to B to B to C or let's do a general overview. Like, how do you see the focus shifting from those between those stages and yourself adapting to them or trying to adapt to them?

Adam Kay: Yeah, I think the first thing was to not think about these stages as milestones or as endpoints. They were injections on our journey to help us in that stage of growth. I'd argue some may have better been avoided in hindsight. I mean, we now know about the overvaluation of the VC world. And I think a lot of it, it feels like just automatic muscle memory of, hey, well, I need to go from my series A through to series D to series E to exit. And that's the route. I think for me, again, one of my strengths has always been that I look at things differently. And I remember when I was an AE inheriting an account that a previous AE had worked and my initial thought was I can do this better. And I think that's quite misplaced, obviously, but it is something that has an intrinsic confidence inside of me. So I kind of put the fundraising to a side, of course, working closely with our CFO, knowing how much runway we had, knowing how much budget we had, knowing what our revenue had to be to kind of make sure we had enough runway was very important. Um, but I think it's the same thing, regardless of where you are on stage and you know, the stage of business that I typically like to join is when the business is transitioning away from a founder-led sales motion. When you've got a founder who's, who's kind of developed a kind of a notion of product market fit has got kind of a bunch of clients on boards and, you know, again, Harrison, the founder done an incredible job of really kind of working through at that time, what was the kind of the Mac and the PC app development community, which was Paddle's ICP. I think the mandate was clear to me, which was to get us back to triple digit growth. It wasn't to get us to 100 million in five years. It didn't get us to series D, it was growth. And ultimately if you grow and you grow healthily, then generally a lot of the other problems look after themselves. So how do we do that? Well, again, it always starts with, what is your total addressable market? Who are we targeting? What's your ICP? Um, how many are there? What's the competitive landscape and building that go-to-market? When I joined, we changed the ICP. We changed the go-to-market away from what was kind of a PC and app development community of downloadable software into the world of SaaS. And that was the first transition that we did away from this downloadable market. And again, it wasn't a very difficult decision. I was being told time and time again, we didn't have product market fit for SaaS. I looked at our customer base and I realized 20, 25% of our existing customers were SaaS businesses. And so I turned to my colleague, the VP of CS, and I said, we must have a major churn problem coming up. And she replied, well, we have never churned a customer. So I said, do we know what the market fit is? Like, you know, we're just not targeting them, but we do have a fit for what they need there. So we really focused on that. And the first thing that I really focused on is about repeatability. You know, again, the story of Pado is wonderful. The proudest data point that I have on that story is we grew to that revenue size and through all that funding with 150 people. We were not a big company. We did it very lean. We were always looking at ways to automate things and create efficiencies. Even though we weren't thinking like most businesses are today, which is about margin and profitability, we were always thinking, and this was something Christie and the CEO really embedded in us, which is that we don't celebrate hiring. Hiring means it's a failure on us that we were unable to do this with the resources we had available to us beforehand. And I've really taken that as a-

Alper Yurder: Wow, how different. Can you repeat that? How does he see hiring?

Adam Kay: It says we don't celebrate hiring. And again, with due respect, I know there's lots of posts out there saying, Hey, our thousandth employee, our 20,000th employee. We looked at every additional headcount as a failure on our part to be able to solve a problem through automation and, and efficiency. So, and again, fast forward to where I am now in a bootstrap business, it's really kind of created that DNA of trying to figure things out without throwing money or people at them. So that was the challenge and we had to really...

Alper Yurder: That must be a very fresh way of thinking for a lot of people whose default was just throwing money at problems and even in life I think a lot of us are trying to throw money at problems. I have a specific question. What fascinates me is I always really like the idea that you explained it. I didn't see it as like, you know, A to B to B to C, whatever. It was an injection into what we're trying to achieve. That's all good. But the expectation of your investor changes and the expectation of your team, probably, like how they see success, that changes as well, doesn't it? Like how you view it, you know, a 10k account was a big win in the beginning and now like two million accounts is now, I don't know, I'm making up. Like we're the deal size is getting larger, brand names getting fancier, sales cycles longer and how was that impacting you and the team?

Adam Kay: So again, I think it had helped that we'd really drained dry our serviceable addressable market, i.e. the downloadable software markets, which we've been through for the last four years. And that was a big reason why growth was plateauing. I think by going off to this new market, we had to really think about segmentation. And one of the first things that I did was, and again, this ties into the other strategy of mine, which I'll touch on in a second, but I split the team out into a kind of an SMB and mid market team. Um, two reasons. One is both required a different touch, a different approach, different value proposition, um, and of course, different expectations in terms of predictability, sales cycles, um, kind of cat to LTV, et cetera. But the other part for me, which is perhaps much, much more important, which was my playbook is around hiring very inexperienced people, putting them in on the ground floor, which is typically kind of the SDR, what I call the academy seeing who swims and sinks, investing in the people who are swimming and building a career path for them within the business so that you can go from SMB SDR to mid-market SDR to SMB AE to mid-market AE and you are progressing through kind of the seniority or kind of the size and value you're delivering back to the business there. So I'm a big fan of creating these career paths because people are the business and the business is the people and there isn't much more to find.

Alper Yurder: That's very difficult as opposed to hiring and firing. Or actually, to be honest, I am being the devil's advocate. I completely agree with that, because if you go through the hustle of hiring once, why try to, you know, replace that person, just retain them and improve them and whatever. But most people prefer the other.

Adam Kay: Yeah, but also don't be so wed to that philosophy. We bake into our model that 30% of SDRs we hire won't make it past six months. And whilst you should always be improving your processes for kind of attracting and identifying talent, you're going to get it wrong. It's going to happen. But for me, the risk to the business, the cost to the business, the risk to the other people was much lower if you got it wrong at the ground level, then hiring senior AEs, which again, I learned, I did. I hired tenured seasoned AEs on top salaries who completely failed in the business. They were coming from a very mature, predictable environment to almost chaos at Paddle. And I needed a certain type of person to cut through a lot of the noise. And it took me a while to figure that out.

Alper Yurder: Why? Oh, I love that. Can you tell us what's the type of person that cuts through the noise in this high, high-paced? I don't know when I say high velocity because I don't know the product that well, but, you know, as opposed to a very established, like, long-stay cycle environment, like, what makes or breaks the person?

Adam Kay: Well, it's easy to describe. It's hard to identify. And it's probably still a lot in progress, but I think for me, it's somebody who's comfortable with change. In fact, I'd go even further and say somebody who thrives with change. Um, and doesn't, and somebody who's not scared to try things and to shine a light on their success and failure. Um, somebody who is intrinsically commercial has a commercial mindset. They're not just there to follow a playbook. They understand the value proposition. They understand the pain. Um, and then somebody who is obsessed with growth. And I don't mean somebody who's always pushing you for promotion. I mean, that's part and parcel of what they're going to be doing and asking for more money, but actually somebody who really takes it upon themselves to learn, to develop and not just exclusively reliant on their manager or their HR team to develop and train them. So. you know, the types of people that will send me a podcast or an article on LinkedIn at 11 o'clock at night, because naturally that's what they like listening to and want to develop themselves. People who harass me for books they should read or podcasts they should listen to. Um, that's the type of behavior that for me not only says you thrive in this environment, but you're actually probably a future leader that I need to invest in as this business scales, you're going to play a more and more important part.

Alper Yurder: Hmm, yeah, in order not to get the work-life balance hate, what do I have? What's the politically correct way of saying this? Okay, I agree. I agree, and I think I wanna be with people who are curious, interested, you know, harass, exactly, in that word. Like, this is the drive that I get from talking to my head of content on a daily basis. This is the drive that I get from talking to a successful client. Let's try to figure things out together, curious, interested, excited. But then of course, work life balance, whatever, it becomes blurry. Like, what would you say to somebody who says, listening to this podcast and saying like, why am I sending you a link at 11? That's my meantime, you know, just to be again, devil's advocate a little.

Adam Kay: I think two things about it. Firstly, what I mean by that is, maybe this is wrong, and I have been shouted down. We've spoken about networking groups before. I've been kind of attacked on these networking groups, but I like those people who choose their me time to be the same as their professional development. The same way when I was a kid and I was looking through the pages in the Times and the Share pages, that didn't work. I was curious, I was interested, I was growing, I was learning about businesses and ownership. And I think if you can find those people who are truly inspired and energized by the work that they're doing, how lucky are they? They don't look at this like, oh, this is work time, this is me time. Now, there's a different challenge because they don't know when to stop and they need to be told, go take some holiday. Stop talking to me. Stop messaging me, you're going to a beach for two weeks and I don't want to hear from you and it's really tough to send them away but again that's as a manager's job you've got yeah I can see your performances is waning I can see that your energy is draining I can see your eyes are bloodshot stop you know stop and take some time but this whole kind of work-life balance argument again for me we're in a startup

Alper Yurder: Yeah, you're sick, you need to take time off.

Adam Kay: We're not predictable. We don't know what's going to happen. And yet the people who kind of do not just kind of the clockwork, cause that was my life in law. My life in law was the people who were there or seen to be there, the latest are promoted. It Doesn't matter how good you are, but I do recognize in a startup environment, when there's so many jobs to be done, people who step out of their lane and into other responsibilities and seize vacuums of that kind of responsibility, they are the ones who go further. Does that mean that the people who don't will be fired? No, of course not. I like to talk about my best friend. Him and I started our sales careers at the same time. He is an AE. Why? Is he any worse than me? No, he's actually a much better salesperson than me and probably a much, much better manager and leader than I am, but he doesn't want it. He wants to finish at five though. He's making a ton of money. He's making a ton of money and he's happy and he goes out with his wife every evening and he puts his kids to bed every day.

Alper Yurder: He might be making more money at times as well. With the big commission checks. Love it.

Adam Kay: And that's the life he has chosen. And I only have respect for him, but he's not working in a startup that's trying to get to $100 million in the first five years.

Alper Yurder: Yeah, choices. I completed it. I mean, yeah, there could be a whole episode from this. So coming to say let's talk about some of the current issues you tackle, Adam. You're building and scaling the business and you're doing it all bootstrap, if I'm not mistaken. OK, can you tell us a little bit about that experience? Now you don't have that VC pressure or whatever. Does that differ in any way?

Adam Kay: That is correct. Well, we talked about hairlines before. So I call this kind of, this is my VC hairline, this is my bootstrap hairline. I, yeah, I mean, look, when I left Paddle, I deliberately chose to go into a non VC backed world for several reasons, partly because I saw the storm clouds forming, but also I wanted to test myself. I've never worked in a bootstrap environment, only in a VC backed environment. And I wanted to see if I could do it again without the bags of cash available to you. Is there pressure? Yeah, we are much poorer than VC backed businesses, but our ambition is just as high. I am looking to grow the business triple every single year and we've done very well until now. But yeah, the pressure comes in that we can't throw money at problems. We've got to think very, very cautiously about our budgets. We are forced to think about new ways to do the same things. We've come up with some great innovations that have enabled us to do so. And I think it makes us a much better business as a result of it.

Alper Yurder: Yeah. And actually you thrive in an incredibly crowded market space in terms of competition, you know, gaining market share, etc. That must be all very hard. Are those things that are sort of top of head for you or what's top of head for you at the moment?

Adam Kay: Absolutely. Well, growth is growth, right? But I think again, from my experience and what I'm seeing in the marketplace, a lot of our competitors are very much focused on logo acquisition as their growth driver. And the employer of record space, it's a very simple model. It's a monthly recurring fee for every employee that you ask us to employ or mandate us to employ on your behalf. Meaning, actually, we don't have to spend so much on top of funnel logo acquisition if we do really well by our customers, because if we choose the right customers and do well by them, they're going to grow and they're going to put more employees onto our platform and they're not going to churn because we provide a great service. And therefore we need to really focus on, well, what do we need to do to really make sure our customers are happy? So, you know, coming from a sales background to now more of a kind of a broader revenue leadership background. I've really de-emphasized the point of sales. Look, sales and new logos are really important. But actually finding the right customer, in fact, put it this way, 70% of our revenue growth this year is expected to come from existing clients, not from new logos. And that means I can structure the team based around that model. I can structure the team to be really focused on support, on success. Our sales team is very small.

Alper Yurder: Oh wow. Okay.

Adam Kay: Um, our SDR team, you know, we're very, very selective and very intense in terms of training and promotion there. Um, but it really helps us kind of think about the capital allocation within the business to achieve our outcomes there. As opposed to again, probably being a bit thoughtless in previous roles where we're like, well, we need a big sales team and the more sales teams we have, the more customers we have, therefore we need a big success team and a big support team. And actually asking yourself why. What are we trying to achieve and is there another way to do this? I think it's a really important way to do it. Okay, so what's the journey of the buyer like from the moment that you have first contact with them? How does it work for your buyers? And why are they happy?

Adam Kay: So our buying, well, again, I think we've got to be looking at, you look at the market, the EOR market, and there's some very, very big players out there who've grown very, very large over the last few years, taken on a ton of funding and have really kind of accelerated away. But by and large, and I know the model did exist pre-pandemic, it was the pandemic that gave birth to this industry. The pandemic that massively accelerated. So no one's really got more than four years experience and people are still figuring stuff out. For me, a small business is much better at figuring things out than a big business. We're able to pivot, we're able to kind of iterate faster. And so I think as a result of being last to market, we've been able to learn what matters and what doesn't matter. And, you know, and so when I joined the business, this was what was plaguing me when I joined, which is why are we different? You know, our metrics were absurd and we've been trading for 12 months. We'd already passed the million dollars mark within the first 12 months. So pretty insane from a standing start there. Um, but I didn't understand what was different about our offering. Um, and I spoke to a lot of people in my network, a lot of our clients as any good kind of revenue leader will do when they first start saying, what do you like about us, what do you dislike? And it just kept coming back to the same point that really. The people that pay the bill, the employer who is our client, doesn't really mind which EOR they use. What they really care about is their measure of success is what is the experience for my employee? How does my employee feel about you? Because again, we're talking to HR folk who understand that the best businesses are built on the best people. And if you look after the people, the business will, it's a lot easier to be successful. So what's, and I looked around the market, no one is focusing on the employee. No one is focusing on the employee experience from candidacy to offboarding. That experience should be premium. Why? Because it reflects on their employer and of course reflects the sentiment of the employer to us. So we are what's called the first employee first EOR. We are absolutely obsessed with our service level, our response time, our accuracy of payments, and less so in terms of acquiring these big, sexy, kinds of shiny logos.

Alper Yurder: All right, so what does that mean in terms of... I get all of that, fine, but at the end of the day, you still have a buyer in front of you, which you need to impress. And I'm imagining if I am an HR or recruitment or employee engagement, whatever, you know, a lot of admin, a lot of tasks, a lot of complexities. And then there's these five guys pitching to me, similar products, etc. So you explain the value to the end users, and I'm sure they buy part of it, but how do you make life easier for the buyer? Like, do you provide, for example, does your client's success come early into the conversation? Do you run demos and then two weeks later, somebody randomly follows up? Like, what is that process? Because I've had a lot of experience with EOR providers. That's actually where I'm trying to come from in a very political way and some of that was really frustrating as a buyer. So how do you differentiate in that experience you provide?

Adam Kay: We deliver a customized process for each buyer. So and again, people are probably thinking, well, hold on, that's not scalable. You can't customize every single sales journey, but actually the key to it is identifying which accounts we want to target in the first place. And again, part of the blessing and the curse of the EOR market is our TAM, our total addressable market is infinite. I mean, it's the whole world, every company of every size, every country, who is open to hiring remote businesses and not setting up entities there. But that's also a bit of a curse because if we think about scale, it's a, you which is probably kind of the most famous book around this, which focuses on a clear segment, absolutely nails that segment and expands out from there. So we've really kind of done a lot of work in the first 12 months that I've been here, which is around defining our ICP, evolving from total addressable market to serviceable addressable market to serviceable obtainable market, and identifying a bunch of accounts that fit what we're trying to do. And again, you know, when I joined, with all due respect, we're scraping lists from Crunchbase and LinkedIn and just kind of spreading spray and pray. But we're doing a lot of intelligence now. And we're working with some really, really intelligent partners to use data, be that kind of technographic, thermographic, demographic data to say, can you find every single company that fits within our ICP? We're predominantly at the moment focusing our outbound efforts on European, African, and Middle Eastern businesses, sub two and a half thousand employees. For a whole bunch of reasons, but predominantly that's where we believe we can provide the best service. There's no kind of time zone issues for us, we're able to support each other from a language perspective. But ultimately identifying which of those companies that fall into that bracket are currently hiring remote roles, what roles are they hiring for, and how can we differentiate ourselves in terms of our approach there. Once we've got that hook, we introduce an AE very quickly onto the call, and we need to determine and work with our prospect to determine what are the criteria we're going to be using, because like you, presumably, you're not just looking at us. We don't own the segment. So what are the criteria? Well, price is always one of them. And I never like going to battle on price. Price is not a defensible value proposition, especially when you're competing with businesses who've got much deeper pockets than you do. Our product is great, it's slick, it's very easy to use, but it doesn't have all the bells and whistles and all the cool stuff that others do. So what are the other criteria? So this is when we work with our prospects to really say, well, if you're looking at the same product and the same price, how are you going to decide? And this is where we really start to, it's almost a challenge of sales methodology to say, this is what we think your criteria should be and this is why it matters to you. 

Alper Yurder: Oh, I love that.

Adam Kay: And then it's on the sales rep to A, get buy-in from the prospect that these are the criteria that matter to them. And then to prove that we are able to deliver against those criteria. And I think salespeople need to recognize they're not trusted. People do not trust salespeople. People know we are paid a commission. People know we are paid to close deals, which is why, again, a great salesperson will look at the resources and people around them and say, what is the best approach for this deal? Is it bringing CS in? Is it bringing an executive sponsor? Is it running a product demo? Don't just take my word for it. Speak to one of our clients, right? And I'm not into American sports that much, but I always call the aid a quarterback. You're not gonna score the touchdown necessarily, but you're going to orchestrate the play. And that's what I'm kind of really pushing our team to do.

Alper Yurder: Okay, love all of the above. I mean, there's so much to deep dive into. I think we'll need another show at some point, Adam, to dive into some of the specifics that you covered today. But in a nutshell, standing out from the crowd is impossible. I mean, it's not difficult anymore, it's impossible. So how do you make that impossible possibility? It's by defining who you're gonna sell to and sticking to your gun, saying like, this is my ICP, this is the best service that… I will provide for them and I will just make sure that I can provide for them. That's why you narrow down the ICP and you give a stellar service as far as I understand.

Adam Kay: I'll challenge that a little bit, Alpa, which is sticking to your guns, I think is a very high risk strategy. Um, I think it's actually having the vulnerability to say, how do we get better at identifying ICP? It's never a job that you're finished. Right. Um, and so what are the leading indicators? What are the lagging indicators to set up to say, are we targeting the right company with the right message at the right time, and how do I continuously test and prove a hypothesis against that? Because if I can.

Alper Yurder: That's a better way.

Adam Kay: Create a demo or a first meeting with 4% of the accounts that I distribute to my SDR team, how do I get that to 4.5%? Because everything's staying equal. If I can increase that rate, then from a revenue perspective, if conversion rates stay the same and ACVs stay the same, that's a huge impact. So our revenue operations team and myself and the sales leadership and the SDR leadership are obsessed with that metric. We call it an account to demo, which is...

Alper Yurder: That's already when, yeah.

Adam Kay: Of the accounts distributed, how many first calls do we get in? And how do we improve that? It's actually one of the key metrics we're measuring our SDR team individually on. Not on the gross number of meetings they create, but of the accounts we've distributed, how many, how many first calls have they got from those?

Alper Yurder: Excellent. Well, our time is coming to the end and I haven't been a good therapist today to cut us in time. But I'm gonna do this anyway as a closing remark. I have two questions, one I'm gonna ask your closing remark on. Do you know What you think you want to talk to our audience about and the second one? In terms of our space by enabling digital sales rooms and your team have used flow have experienced it themselves Like how do you see this space? What's your experience of it? If you have any? Yeah, I wanna get your prospectus on those too.

Adam Kay: So I'll answer the first question first, which is, this is a tough job. This is not a job that you can just turn up, do, say a few things and hope to do well in it. You've really got to commit to this and it is hard. It is wrought with failure. But if you are open to growing and open to really kind of developing yourself, the sky is the limit and you can have a very, very exciting career, um, you know, and a very lucrative career if you follow that, but don't, don't be too proud to say this isn't for me. And don't be too proud to do it if you're not enjoying it because a salesperson is a rare breed and I truly believe you should enjoy the hours in which you're working. Okay. Not every day you'll have bad days, you have bad hours, but by and large enjoy your job. It makes it so much easier to do a job when you are enjoying the day in, day out of it.

Alper Yurder: You can't do it any other way and be successful anyway. So yeah, the job will tell you.

Adam Kay: I know that's really basic, but I just think people forget that all too often and try to kind of project what they want to be in and work backwards from there rather than enjoy the ride because the ride will be over at some point and then what. Buyer enablement. It's a really interesting topic and it's one of those kinds of really fast moving segments and industries that our buyers are becoming wiser. There is a…huge amount of resources that every buyer has available to them, but they never had before. And I think every business should be leveraging opportunities to create those efficiencies, to create a better experience for their buyer, but not at the cost of human relationships. It should be there to serve the human relationship rather than to replace it. And I think again, people have this over-reliance on technology.

Alper Yurder: completely.

Adam Kay: rather than understanding how to deploy and enable themselves with it so that they are better at their jobs. So, you know, floaters are a wonderful solution. Um, as are all the other kinds of great new technologies that have kind of entered the sales, uh, tech space and, uh, and, you know, understanding that whole kind of ecosystem, the key really is unless the bots come tomorrow and replace us all, which, you know, one day they will obviously. Um, humans still like to buy from humans. And I'm going to kind of stick to my guns on that one, despite saying that we should never stick to our guns and say authentic relationships, integrity and credibility cannot be replaced by technology, but can be enhanced by technology if you're using it appropriately.

Alper Yurder: can be enhanced, can be empowered, can be enabled. You know, if you have a sales companion like a floater or whatever, that's just a better way of selling, but it's not going to replace you as the human because, you know, you will build the relationship that's based on trust with your buyer. That was a wonderful show. Thank you so much, Adam. I think it's been one of the longest recordings I had because it was just... Don't apologize. It's my job to cut and I'm never good at it. Because when I'm hearing good stuff, I don't feel like cutting anybody.

Adam Kay: I'm sorry, it took a long time.

Alper Yurder: Thank you for being here with us, Adam. And if you enjoy the show, this was yet another episode of Sales Therapy. You can subscribe to us on YouTube and your favorite podcast platform. And we'll be having plenty of more conversations with them with Adam in the coming, I think, months and years, hopefully. And thank you very much for listening. Bye bye.

Adam Kay: Thank you for having me. It's great to be here. Bye, Alper. Take care.

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