January 3, 2024

Closing Deals with Confidence: A Sales Strategy Deep Dive with Akiva Weiss

In this episode of Sales Therapy, Alper and Akiva dive into how to manage high-stakes client relationships and navigate complex deals.

Table of contents

Meet our guest

Akiva Weiss, CEO and founder of Copilot, a GTM strategy consultancy for early-stage startups. 

With over a decade of experience in B2B sales, business development, and digital marketing, Akiva is passionate about helping startups go from 0 to 1. As the CEO and Founder of Copilot, he provides GTM strategy for startups looking to enter a new market.

Key takeaways

  1. For early-stage startup success, establishing connections and engaging in commercial conversations are crucial, especially in securing a spot in the next year's budget.
  2. Google's email limit changes present an opportunity for salespeople to focus on value-driven interactions, strategic partnerships, and move away from traditional mass outreach methods.
  3. Successful complex sales require expertise in the client's industry and problems; adopting consultative strategies and continuous alignment on pain points trumps traditional urgency tactics.
  4. Challenge the assumption that delayed sales indicate problems; aligning timelines during the discovery phase and documenting agreements for reference are vital for successful deals.
  5. Salespeople must balance deal closure efforts with proactive top-of-funnel engagement, emphasizing the value of active involvement in customer relationship management for sustained success.

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If you’re too busy to listen to the whole episode, here is a summary of the conversation with some key highlights for you to skim through 👇

Navigating entrepreneurship and sales challenges

In the first 5 minutes, Akiva shares his entrepreneurial journey with Copilot, the company he is currently building. As a solopreneur, he’s handling sales, delivery, and various tasks himself, with some help from several contractors. The current service line in his consultancy company includes customer discovery, product analysis, and demand generation services.

Akiva mentions the common challenge for early-stage startup founder to secure a position in the 2024 budget and emphasizes the importance of making connections and engaging in commercial conversations with potential targets.

“I think everybody right now is trying to get into the 2024 budget, at least trying to get on the radar and make sure that those connections are being made.”

As Alper raises the question of other common challenges in the sales space for 2024, or rather his predictions, Akiva refers to the changes made by Google in terms of email sending limits aimed to fight mass outreach. He doesn’t see that as a problem and assumes that “there's been a little bit too much spam activity” so he sees this change as an opportunity for salespeople.

“And I think that right now until people kind of reset and inboxes become less spammy and more about value, I think that there is a lot of opportunity to do sales motions outside of just sending cold emails.”

Akiva anticipates a future where successful sales strategies involve partnerships with marketing and a focus on value-driven interactions, moving away from the conventional spray-and-pray approach.

Closing complex multimillion deals

As Alper shifts the conversation to complex sales, Akiva admits that they are very hard and cause a lot of stress. He shares a story about a friend who got exposed to the world of enterprise sales with multiple stakeholders after being in transactional selling and was completely blown away. 

He also shares his observations on how similar complex selling is to consultancy. Because to win complex deals, it’s not enough to be a product expert, according to Akiva:

“You're going to fall flat if you're a product expert. What you really need to be is an expert in the industry, an expert in the problems that your customer is trying to solve, and an expert in what their leadership and strategic vision of their leadership is and how you could help them get there with your product. So it's not about your products, it's about them.”

Speaking of tactics that can help close those complex deals, Akiva mentions the Challenger sale methodology and the “teach, tailor, take control” approach. He reflects on his tenure, noting that as he spent more time in the role, he became more confident and adept at anticipating and understanding the problems clients might face.

At the same time, Akiva advocates against traditional urgency tactics like end-of-quarter discounts, favoring a more sustainable approach. He suggests continuous alignment with clients on pain points and solutions, emphasizing the importance of consultative strategies. 

“I think that the better tactic is really to just continue to circle back to your discovery, make sure that everybody is continuously aligned on what the pain point is that we're solving and what we talked about in our discovery around the urgency of that pain point, of solving that pain point.”

He discusses the common assumption that delays in sales indicate problems, challenging this notion by sharing examples of successfully closed complex deals that took longer than expected due to insufficient initial exploration. In this regard, Akiva emphasizes the importance of aligning timelines during the discovery phase and ensuring documentation for reference. 

Convergence of sales roles

Akiva goes on to reflect on the significance of focusing on top-of-funnel activities, a lesson from past roles where he was deeply involved in complex deals, urging salespeople to balance deal closure efforts with proactive top-of-funnel engagement for sustained success.

“I would urge all salespeople to really think about balancing that time between, you know, making sure that you're in the weeds of getting your deals over the line and, and being consultative to your, to your prospects or to your stakeholders, but also filling that top of the funnel.”

He also underscores the value of active involvement in customer relationship management and customer success, as it can lead to upsells, renewals, and continued relationship-building within the organization. Ultimately, the focus is on transforming a customer into a long-term revenue source and referral channel through sustained engagement and value addition.

Moreover, an effective salesperson might sometimes need to act as a co-founder, particularly because many technical founders lack the skills to navigate the market, generate leads, and create demand.

“I think that a lot of the technical founders, they don't know how to go to market and they don't know how to, when there's no leads that's coming to you, they don't know how to go out and grab their own leads and create their own demand. And, and that's a skill. And I think that that's, that's something that every founder has to have.”

Rapid-fire questions

  1. As a leader, what's your top priority when you're leading a team? What's the one thing that you value most about leading?

“The thing that I value most about leading is giving autonomy to the individual. I want them to be collaborators with me and I want them to essentially be adding what I don't have and very senior, so somebody who could own their domain, who could advise me and help me as we're crafting the convergent spaces between what we're working on, almost like very peers to an extent.”

  1. How do you create urgency and how do you make sure that the deal flows smoothly?

“I think it all comes down to really good discovery and really good project management. So I think that it's about going back to the pain point and the urgency and the timeline that you've discussed, understanding what it's blocking, what it's not, and when that has to happen in order for the strategy to move forward.”

  1. What type of objections do you generally hear from, or have you heard in your career from clients and how did you overcome them?

“Obviously pricing is always an objection that you have. And it's always about realigning to value. I want to try and show them that their budget isn't necessarily aligning.”

Resources:

Full episode transcript

Alper Yurder: Great, so today I'm with my friend Akiva, Akiva Weiss. He is the founder of Copilot and he helps early-stage founders go to market. Akiva has over a decade of B2B SaaS sales experience and we work together in many complex deals. So we got a lot of things to share today. Akiva, welcome to the show. We've had so many hiccups trying to record this episode. So I think this is gonna be great. Like, absolutely. I think...

Akiva Weiss: We should do a bloopers reel.

Alper Yurder: Our content manager is going to really enjoy watching the bloopers episodes where we're trying to get to it and we can't. But I think this one, it will be lucky. Excellent. So how are you feeling today?

Akiva Weiss: So far so good, can't complain. But if you want me to, I can, but I won't.

Alper Yurder: Yeah, we'll definitely get into the complaining part. I mean, if I get started, we'll never end. But so let's give a little bit of background about Akiva Weiss. For anyone listening, I like to start these conversations with a bit of like, where did you grow up? How was your childhood? Because any therapist starts with that, right? So tell us about younger Akiva.

Akiva Weiss: Yeah, I grew up right outside of New York. I went to school and everything all in New York. So I lived there my entire life. I started my career actually as I was exiting college. I was still in college. I started in the mailroom of a company that did server maintenance and server sales. It was a very interesting place to be at. And I worked my way from the mailroom to an analyst role. And then eventually,

Alper Yurder: Thanks.

Akiva Weiss: Went to a marketing role and then into sales. And so that's how my career progressed. It was probably a lot different than most, but now I'm living the life, founder life.

Alper Yurder: Living the founder life. Look at us. Excellent. And where are you currently based?

Akiva Weiss: Currently based in Phoenix, Arizona.

Alper Yurder: Do you want to share the story about that? Very shortly, maybe.

Akiva Weiss: Yeah, very quickly. I went to Arizona early, early pandemic, thought we were going to be here for two weeks, literally packed a backpack. It ended up being that my wife was pregnant with our first child and we've been here ever since. So yeah, it was definitely a turn of events.

Alper Yurder: Yeah. It's the story of many city dwellers during the times of COVID, I think. They went to the urban landscape and they stayed there forever, happily ever after. Excellent. And what are you working on these days? What's good?

Akiva Weiss: So yeah, Copilot is the number one priority, trying to build that business. Right now, I'm somewhat of a solopreneur. So I both do the sales, delivery, everything myself. I have a number of contractors that I work with. So I have one contractor that's working me right now on a particular deal. And then I have a few other contractors that work on other types of products that I sell. So I have a service line that includes customer discovery with making sure that the problem and the product and the market are right. And then we also have a product analysis service, which is really a product expert goes into deep dive on product recommendations. And then the last is demand generation. So that's a marketer that I work with does demand generation.

Alper Yurder: Excellent. And you work with founders and sales leaders. Actually, we've worked in complex deals and we'll get into it. Back in the day is trying to close multi-stakeholder deals and going through all the hopes, but currently we're working a bit more kind of like early-stage founders and how is that like what's top of mind for them? What are they looking at as we enter 2024?

Akiva Weiss: Yeah, I think everybody right now is trying to get into the 2024 budget, at least trying to get on the radar and make sure that those connections are being made. So, you know, as I'm doing customer discovery with some of my founders, we're also trying to figure out who is a really good target to go back to and actually start engaging in a commercial conversation. So that's very much top of mind right now. And thankfully we've had a lot of conversations and I think a lot of good meat on the bone over there. So we're gonna be starting that motion right now, imminently.

Alper Yurder: Okay. Okay, so it's grabbing attention and being under the radar, I guess, right? Or maybe reviving old conversations.

Akiva Weiss: Yeah, you know, it's a little bit different for us because we go into our conversations with just trying to understand what's, it is very similar to a discovery conversation, just framed a little bit differently. But, you know, after those conversations are had, and we see that there is interest, at least in solving the problem, the way that we describe the product sounds interesting to them. I think there's a lot of opportunity to go back.

Alper Yurder: Yeah, anyway.

Akiva Weiss: And say, hey, we figured out what we're doing now. We wanna continue that conversation in a more commercial capacity.

Alper Yurder: And do you have any already like kind of predictions or anything that you're seeing is becoming really hot in the space of sales tech or sales world in general and any predictions for 2024?

Akiva Weiss: Yeah, I have my own perspective here. I definitely think, I mean, there's a lot of chatter about the changes that Google is making to email. Um, you know, looking at it, I think you have to be sending 5,000 emails a day. So I honestly don't know who's sending that many emails. And if you're, if you are, you are sending spam, so you should be blocked. Um, but I think that that has really poisoned the well a little bit. Maybe there's been a little bit too much spam activity. And I think that right now until people kind of reset and inboxes become less spammy and more about value, I think that there is a lot of opportunity to do sales motions outside of just sending cold emails. And I'm talking about top of funnel. So ways to think about sales through a partnership lens, ways to think about sales as partnerships with marketing, creating, giving marketing that really good insight into the conversations that you're having, who the right targets are, making sure you're creating those sales qualified leads faster in that partnership capacity. So that's kind of where I'm thinking. I'm thinking about other channels, multi-channel sales, leveraging LinkedIn a lot, potentially even leveraging things like Twitter. I think that creating your own personal brand is really, really important these days and actually trying to drive awareness of your own self as a salesperson. That's something that I think is something that's really important these days.

Alper Yurder: Yeah, I completely agree. And I think a lot of mass spray-and-pray killed, yeah, it poisons the well, definitely. I think it's, it's become a bit like, symptomatic of, high velocity, low-ticket, businesses. It, I guess, early on, but then it's spread it to the rest of the industry. Whether you're selling something tag, non-tag, it doesn't matter, but you and I are quite used to those long sales cycles, you know, a handful of key accounts that we want to kind of enchant and make sure that we're closing those deals and complex multi-stakeholder. We come from that world, so we're a bit more used to, I guess, the difficulty of it's a bit more than just sending an email, right?

Akiva Weiss: Yeah, I think it was a lot less spray and pray for us in our roles. But, you know, I think that you're right. The burgeoning like tech sector and SaaS and like they were, that was really, that was a big bubble that now is contracted a little bit, but still now we're hopefully resetting. There's obviously a lot of value in SaaS startups. Um, but there was just a lot, a lot of action. I think that emails were just becoming spammy because, as you said, low ticket, SaaS is just about getting customers as much volume as possible, really did poison the well. So I think that these changes are good, good changes. I think ultimately things will reset, email will be back to normal. So this is, I welcome the change.

Alper Yurder: Yeah, I completely agree. I think there's a lot that the world learned from the playbook of that tech sales and the sales playbook, high velocity, process driven, qualified, disqualified, Hunter brings in the lead and then just hands them over to client success to close the deal, et cetera. The way I started sales and I think the teams that I built have always been nurturers and long sales cycle, very educational, very consultative selling. So that's no stranger to us. And I think the tech world is now adapting to that world. I had two chats today and they were all about, you know, how do we change the mentality? How do we create a bit more cognitive awareness with salespeople? So they're not just thinking of the next demo, but they're actually a bit more invested and advisors. So quality over quantity. I want to dive into that because as I say, let's talk about, let's not preach, let's talk about what we actually did. When it comes to closing complex deals, let's make an entrance there. How do you feel about complex deals? Let's start with that first, like big client relationships, multi-million dollar deals. How do all those things make you feel?

Akiva Weiss: Um, stressed. They're hard. They're really hard. You know, it's funny. I have a friend who he's, he entered the world of sales very late, actually, just lit this year or last year. And I knew I actually was the person that put him in touch with the sales manager who was reaching out to me. And I said, no, I'm not the person you want. You want this person became instantly the number one salesperson of the company, but he was doing transactional, more transactional sales. And he, you know, I was telling him like, you know what? There was a different type of sale that you're not familiar with. And just so you know, what you're doing right now is great. And I'm so glad that it's working. I knew it would. I knew that was your personality type, but I just want to make you aware of this other type of sale. And he got exposure to it. And he's like, whoa, this is a whole different universe.

Alper Yurder: Excellent.

Akiva Weiss: Um, and it's the universe of enterprise sales, right? It's like real complex, multi, you know, multi-stakeholder. You have a committee of people that have to give input, lots of gatekeepers that in all directions from all parts of the organization and from technology to, you know, the budget holders, all of these different people that are essentially trying to keep you out and you trying to figure out who's the real person that has the influence over here? Who's the real decision-maker over here? How do I actually really extract the real pain point and map my value to them? How do I show in a consultative way that what they're doing is actually leaving money on the table? And that's the world that we really come from, like really looking through 10Ks, doing research on the organization, reading the memos by the CEO to understand where the direction is and being able to come with a perspective about this is where you're going, I know that. This is where I think you guys are missing and here's how I could help you get there. That's the world that we come from and that is the world of complex sales.

Alper Yurder: Yeah. And I love how you explained it. And I think your positive energy and what comes across as you explain it. Cause I really enjoyed, I think, you know, the classical term, the salesperson, the salesman sales guy who the auto vendor type, I think it's, it's always the stigma that comes with this job, but actually what it is, is it's a lot of like being an advisor, somebody that your client can actually trust. I almost see it like a practice lead at a consultancy firm, you know, who has to know about the industry, who has to learn from X and then carry to Y, I guess in a confidential way, of course, but the person who actually is there to up your game, you know, client X, Y.

Akiva Weiss: I couldn't agree more. And I think that was the biggest thing that I probably learned while I was learning the sales role at GA where we came from was how similar those two roles are, how you really have to be not just a product expert, but you have to be an expert in their world. You can't just be a product expert. In fact, that's going to, you're going to fall flat if you're a product expert. What you really need to be is an expert in the industry, an expert in the problems that your customer is trying to solve, and an expert in what their leadership and strategic vision of their leadership is and how you could help them get there with your product. So it's not about your products, it's about them.

Alper Yurder: Yeah. And I think these are learned skills that one can develop over time. If you have the basics, which is curiosity, empathy, if you have a genuine interest in the clients, et cetera, all those skills can develop over time. So I want to go into those skills a little bit. And what do you think you've developed over time? What kind of skills or what kind of tactics that help you to be more successful in, in making those complex deals flow and eventually close?

Akiva Weiss: Yeah, I think the methodology that we were kind of brought up on was the Challenger sale methodology. So it's, you know, teach Taylor take control. And that is, that's really the thing that I learned the most, the thing that I think was most enlightening to me about sales. And I think it goes back to your idea of being like a practice lead, right? That was not the way that I thought that sales would be when I was coming up before. I was actually an account executive and then a senior account executive. That wasn't the way that I thought the sale was. I didn't know anything about it until I read the book and until we started actually practicing and thinking about it internally. It was a massive change in the way that I thought about sales to how sales actually practice in complex deals.

Alper Yurder: Yeah, and it's not just the tactics, but also the, you know, the knowledge, the self-confidence that comes in time with that kind of thing. Like, you do it once, you learn, now you have earned the right to speak a bit more with a client or ask more questions, things that you will be afraid of doing before that you were thinking that could backfire. As you learn things, I think you become a bit more comfortable with yourself and you excel at your game.

Akiva Weiss: Exactly. It's such a good point. And I, yeah, I definitely saw that in myself. The longer, you know, I was actually one of the more tenured people over there and the longer that I was in that role, the more that I've seen, the more problems that I've solved, the more I was able to relate and say, here's what I actually hear. Like, I hear these are the problems and I could tell them their problems before they even tell it to me. And almost confirm with them, like, yeah, you're probably like that, right? It gives you a lot of.

Alper Yurder: Yeah, yeah, the moment it becomes your reality.

Akiva Weiss: It's a lot of confidence, right, to be able to tell somebody, like, I know what your problem is before you even tell me. Yeah.

Alper Yurder: Yeah. I think it's a lot of confidence and you have to do it in a way it doesn't feel cocky, which is why I call it like therapy. Like, you know, the therapist comes into the conversation has probably, you know, seen a lot of people with similar issues and they have an idea. But, you know, you can't be cocky. You have to do your discovery first. Each individual is different with their own issues. So, yeah, absolutely. And how about when it comes to? I think a lot of people are going to do some level of client relationship management, discovery, et cetera, but a lot of people struggle with creating urgency or creating demand or making sure that your product or your service is no longer seen as a nicety but a necessity. So when it comes to those skills, do you have a go-to tactics? How do you create urgency with buyers?

Akiva Weiss: Yeah, good question. You know, I think that some of the tactics that I've seen out there are tactics that I usually eschew. Like I don't really like them. I think the classic tactic is like end of the quarter, like we'll give you a 10% discount, right? Like that's an urgency tactic that I think only bites you in the butt. I think that the better tactic is really to just continue to circle back to your discovery, make sure that everybody is continuously aligned on what the pain point is that we're solving and what we talked about in our discovery around the urgency of that pain point, of solving that pain point. So if you were able to do, you know, show them what good looks like, let's say in a consultative way and show them like. This is the strategy. This is how I could get you here to this strategy. How important is that? What's holding you back? How, like, what is the impact of that on the business? What teams are impacted? You know, like if you could really get to the core of that in your discovery and have clear alignment with your prospect around, yeah, like it would be, if we were able to do this within, you know, it's holding back this project, which we really need to do and like, this is a blocker to that, et cetera, like that's an example, but really align what the core value is accomplishing it right now, you could always go back to that.

Alper Yurder: Yeah, and you're doing it over and over, right? Like with new stakeholders, each meeting, you're going back to the discovery and making sure that we're still aligned, nothing's changed, or if there's a change, let me know. So I don't know it last minute. I'm sure you have examples of that. Do you have like, do you have those heart attack moments where you felt like you've got it all under control and the deal is closing, but suddenly there's like a new stakeholder or something kind of falls apart? Like, do you have any juicy stories you can share?

Akiva Weiss: Yeah, I guess the juiciest story, this is really more on the contracting side. So this was really getting the deal over the line. But I gave when I closed a big deal at GA, it was actually right around the time of my honeymoon. And I gave it over to my boss saying that this is where it's at. Here are the people that are involved. Like I tried laying out the land and saying, like this is when the expectation is that we will close for this reason. And I gave it to him and I went on my honeymoon in Africa. And I remember this was like, this is actually a really sad story, but I was on the beach of Zanzibar and for some stupid reason, I checked my phone. And I saw an email from my boss saying, I can't believe that the work that like, this is so much work still. And like, you know, he was essentially trying to tell me like, this is, we are working really, really hard on getting this closed by this, by the end of the corner. And, and it's, and so maybe, maybe that was partially my fault in like, not actually having really great expectations aligned around what their urgency was and what is really our urgency. But, I also think that was a moment where, you know, I think about it as like, yeah, I do a lot of work. Like, you're right, like, yeah, there is a lot of work and that's why you pay me. And thank you for the appreciation, which, yeah, it was a little bit of a buzzkill on your honeymoon, but yeah, that's a...

Alper Yurder: Yeah. I think those handovers, those situations are always like friction and they can always, I mean, I think it's like Murphy's law, it's almost inevitably will go down and which is kind of, I mean, obviously the story of my life as well, like a line, a line, a line, consensus, and then just to see like things blow up because some email thread somewhere, new person comes out of nowhere. And that's kind of what we're trying to solve with, you know, I think that the whole category of digital sales rooms, flow, etc. are trying to do that, like make sure that everything is in one place. Everybody's on the same page. It's all agreed. It's clear, transparent, etc, etc.

Akiva Weiss: Such a huge value to be able to put, you know, the finance person, the person from legal, the person from that's the, you know, your direct, like all of these people when one and what, like in my example, the time where it's down to contracting, you could actually reference back and say, like, here's the project management timeline that we had getting this. Like, you're the one that's holding this up. This was agreed to by your party. Like, let's like, let's solve this right now. Yeah. I think, I think in terms of…

Alper Yurder: Let's cut the crap.

Akiva Weiss: Yeah, it's a great way to get everybody on the same page, be able to almost project manage in one spot where everybody has visibility. That's a game-changer.

Alper Yurder: Yeah. The more we speak with buyers or the more I speak to also sellers, the more we see like where the main pitfalls are, like what are the common sales rep missteps, like not multithreading enough, not following up in the right time. And I, you know, we're all human. When we need to save ourselves, we're gonna save ourselves first. So sometimes your stakeholders will say, I did it. Well, you know that very well that they didn't. Or you agreed on a certain time or how many times has a salesperson faced? Well, your colleague told me another price, you know, those kinds of situations. So I think they create a lot of friction in those situations. So the antidote for me is always transparency, visibility, and accountability. And I think deal rooms really help both parties with that.

Akiva Weiss: Yeah. Could you imagine how valuable that would have been in the deal that we were working on together across overseas with, it was probably somewhere around a hundred emails on that thread. Maybe some, could you imagine how, how simplified that would have been?

Alper Yurder: Yeah, I see. Fucking what? Yeah, it was definitely like, this was when we were trying to close a multi-million dollar deal with McKinsey, a big consultancy company. And I think it was well over 400 emails or so. And that was about the time when I had the idea for Flola, you know, and I didn't know anything about like digital sales room, mutual x-plant or whatever. I was just doing my job, which is project managing stakeholder alignments, which comes naturally, but sometimes you just need something to help you do that. And that's why we started Fola really. All right, so let me shift the focus to another area, which is also very valuable for salespeople I think. Like what type of insights help us to close deals more? And this can be a bit more of a general chat in the sense that I mentioned some of the sales rep missteps, potentially not doing enough multi-threading, following up this, that, or sharing the latest and the greatest. Those are all human issues that can be fixed. But what happens a lot is you're left in the dark. The buyer is left in the dark. Somewhere in the conversation, you will, almost every deal, you'll be ghosted for at least a little while, and you will feel a little bit in the dark. So I guess my question to you is, what type of insights helps you to close deals? What kind of signals helped you to figure if this is a deal worth investing time in or not?

Akiva Weiss: Yeah, you know, it's interesting because I think that sometimes people might say, the, you know, if something isn't moving according to the schedule, then that means that there's probably something wrong, right? If you're getting ghosted when you're following up a few times, I don't know if necessarily, I would be very curious to look back and see if the correlation is real there. Because I definitely have closed deals that were later than expected, probably because I didn't do my discovery well enough. I didn't really think about making sure that we were on the same timeline in terms of their urgency to close to get this project done. There are certain times where that is certainly true, that I'm getting pushed by the client to try and get it over the line as quickly as possible. There's no question about it. They have an urgency that usually is very, very clear to me that they want to get it done by a certain day because they have a thing that they need to hit a timeline. And so, yeah, maybe that's part of the answer. It goes back to the project management, really making sure that you have that all documented really well, that you could go back to it, that you could point to it, and that you could say, hey, we agreed on the urgency because you were trying to accomplish X by Y date. Is that still the case? And that's probably the biggest thing. The other stuff that I'm really thinking about in order to close more deals is really top of funnel. I think that that's another thing in my career that I could point to as something that I would wish I'd done differently in previous roles, was paying more attention to top of funnel than I was. It was always so I was embedded in these… getting these deals over the line and they were complex and so they took a long time. Oftentimes our deals were six months, a year long. And they were multi-threaded and they had tons of emails on an email chain. And it was about trying to like really make sure that we were getting that urgency and being, and that we were able to, you know, a lot of the times it was also with getting that urgency, not just across the person that we've been talking to, but also to the, to the contracting team, right? Like there's a whole new stakeholder that has their whole new set of projects that are on their, their radar. I'm trying to make sure that we get it over the line from a, you know, legal perspective was another big hurl that we had. I probably didn't pay attention enough to top a funnel while I was managing that. And that's something that I would urge all salespeople to really think about balancing that time between, you know, making sure that you're in the weeds of getting your deals over the line and, and being consultative to your, to your prospects or to your stakeholders, but also filling that top of the funnel.

Alper Yurder: Yeah, I think now these two worlds, which were quite separate in the very structured sales playbook, like, okay, your job as an SDR is to generate leads, your job as an AE is to close, and then client success, you nurture. I think those are all kind of converging into one and more and more salespeople are being asked to actually start doing more business development, not only also help with like the onboarding. It's no longer like here, I sold something, you go and take care of it. But it's like, how can I make myself more available to the client success team as a salesperson and how do I make sure that the client is happy? Because at the end of the day, retention is more important now in many cases than, you know, new business acquisition. So you have to be fully, a full, fullbody salesperson, I guess.

Akiva Weiss: I totally believe that. I think that any really great salesperson allocates some of their time to business development. You have to be hunting on your own. You can't just be relying on the leads that are handed over to you. You have to be developing that middle of the funnel, getting everybody that is interested and has, you know, we've done your discovery with over the line. And then also that, like, that customer relationship management and the customer success role. You have to be in the weeds. You have to be joining those calls. You have to be adding value there. Yeah. It's going to only benefit you in the long run. It allows you to uncover more, you know, like upsells and renews and like really able to actually help you continue that relationship, figure out where else in the organization you should be going to, right? Like if you're able to build that relationship, that person that you sold to is no longer just a dead lead to you. Now there's that now they're a revenue source for you. Now they're… they're almost like an affiliate for you. And that's really a referral source for you rather.

Alper Yurder: Yeah, yeah like the show and tell and how they're going to generate business for you. And if anybody, any sales leaders listening, top earning, especially sales leaders, thinking of starting a new as an SDR, I would highly recommend starting a company via founder, because you're going to be an SDR number one and client success number one and AE and all these skills that you maybe forgot that you had or you have to develop. I think you and I are on that boat, right? Where we have to do all of those things at once.

Akiva Weiss: I, that's why I totally think that like a good salesperson should be a co-founder, right? Because like, I think that a lot of the technical founders, they don't know how to go to market and they don't know how to, when there's no leads that's coming to you, they don't know how to go out and grab their own leads and create their own demand. And, and that's a skill. And I think that that's, that's something that every founder has to have. And if you don't, you have to have a co-founder that does that.

Alper Yurder: Yeah, yeah, I think that's what is in startup lingo, which I'm learning as well. It's called a hustler. They call us a hustler in the perfect founder triangle. We are the hustlers. We are the ones who have to bring in the new business and delight everybody and make sure that people are happy so we can grow, right. Excellent. So as we're coming to the end of the podcast.

Akiva Weiss: Yeah.

Alper Yurder: I have this section I call Fire Rapid Questions, and it is three questions and one minute each. And it's kind of gonna be a summary of our conversation really. Hopefully some practical tips for people who can learn from your experience. So the first one will be as a leader, what's your top priority when you're leading a team? What's the one thing that you value most about leading?

Akiva Weiss: Um, well, I think the thing that I value most about leading is giving autonomy to the individual. You have to like my, my goal for hiring at my company. And right now I'm only at a point where I'm hiring contractors. But the reason that I'm hiring highly paid and highly capable contractors is because I want them to be collaborators with me and I want them to essentially be adding what I don't have and very senior. So somebody who could own their domain, who could advise me and help me as we're crafting the convergent spaces between what we're working on, almost like very peers to an extent. That's where I'm at. I'm not at a point where I'm hiring junior level folks because right now I'm just not at a place where I have the capacity to develop. I need people to be able to be autonomous.

Alper Yurder: Yeah, yeah, no, I think, yeah, I definitely agree. And there's a lot of people coming to the workforce really with those great skills of ownership, but which is another topic. Okay, this is not my time to talk. I will ask the next question. So as a closer, what is your go-to strategy for sealing a deal? How do you create urgency and how do you make sure that the deal flows smoothly?

Akiva Weiss: Yeah, the urgency is, I think it all comes down to really good discovery and really good project management. So I think that it's about going back to the pain point and the urgency and the timeline that you've discussed, understanding what it's blocking, what it's not, and when that has to happen in order for the strategy to move forward.

Alper Yurder: Excellent. And the last question will be about objection handling. If that's something you'd be open to discuss. What type of objections do you generally hear from, or have you heard in your career from clients and how did you overcome them? How did you manage them?

Akiva Weiss: Yeah, I think a typical, you know, obviously pricing is always an objection that you have. And it's always about realigning to value. And so, and my strategy is I'm like, yeah, you could, if you, oh, your price point, we're asking for $60,000. And your price point that you're thinking of is $10,000. Let me just explain, like, that's fine. But I just want to share with you the $10,000 solution. This is what it actually gets you. So that just, I want to try and show them that their budget isn't necessarily aligning. It's like, you know, you're trying to shop for, you know, a Lexus and your budget is really a Corolla or whatever, a Toyota Corolla. Like that's just not gonna, you're not gonna get a Lexus just so you know, which is fine, but you can't try to get a Lexus and have a budget for a Corolla. Yeah.

Alper Yurder: Yeah, I think again, it goes back to honesty and transparency and being an advisor because you're actually sharing knowledge or information that they should be aware of because next person they speak to, they'll tell the same thing. So save them the time. All right. That was excellent. Thank you so much. Thank you so much for joining the conversation Akiva. Is there anything you would like to add before we close the show?

Akiva Weiss: First of all, it was a pleasure. Great seeing you again and great being on this podcast. Yeah, I think the one thing that I'll add is if there are any early stage founders who don't have a sales co-founder and really are thinking about their go-to-market, the one thing that I'll say is really make sure that your problem is solving a need in the market. Which means that you need to do some customer discovery. I see a lot of founders trying to hire their first salesperson, not their co-founder, but a first salesperson well before they validated that the problem they're trying to solve exists, and so I recommend against that. I think that it's much more beneficial to you to figure out if that problem exists first before you sink some money into chasing a problem that might not resonate with your ICP. So, yeah, I think that's it.

Alper Yurder: That's solid advice there. Thank you. Excellent. Our time is over and I'm going to cut you on the clock just like any good therapist. If people want to find you where's the best place to reach out? Is it LinkedIn or somewhere else?

Akiva Weiss: LinkedIn is great. You can email me at akiva@getcopilot.io. And yeah, happy to respond. And the last thing is that I love helping founders. Yeah, I just want, there's a little bit of a delay. I love helping founders. You could reach out to me, whether it's to, you know, discover whether an engagement is right for you or whether it's just to pick my brain. I'm happy to help. So feel free to reach out.

Alper Yurder: Excellent. Thank you, Akiva. Well, that's a wrap on this episode of Sales Therapy. If you enjoy the show, subscribe to us on YouTube and on your favorite podcast platform. I'm your host, Alper Yurder, and thank you for listening. See you next time. Bye.

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