Diving into the intricacies of SaaS sales can feel like uncharted territory, particularly for those not naturally inclined toward selling. In the latest episode of the Sales Therapy podcast, we demystify the essentials of mastering handling complex deals. 

Join us as we unveil practical strategies to excel in SaaS sales and navigate the ever-changing landscape of this dynamic industry.

Meet our guest

Michael Ranmi Akinlé, Revenue Advisor | Sales Director at Clari, the leading revenue intelligence and operations platform.

Michael, one of the founding members of Clari, was born and grew up in Lagos, Nigeria but later moved to the UK. Despite getting a degree in Sports Management and plans to go into football, Michael started his career in recruitment. 

His football coaching background made him an excellent communicator so after a year in recruitment he went into sales — cold business development — and later transitioned into SaaS as an entry-level SDR. Within about a year Michael started leading an SDR team as well as field marketing at Dynamic Signal, an employee communications platform. Later, he joined Clari as one of the first few hires in Europe focusing on pipeline and growth. 

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Or skim through the summary of the conversation along with the key takeaways. 👇

Getting started in consultative SaaS sales 

When Michael first joined Clari, they spent a lot of time trying to establish their ICP in Europe —  understanding which accounts to go after and why they should go after them. This helped them build a territory plan for their sellers to go and execute.

But they first had to do a lot of education and brand awareness, trying to help leaders see how they could do things better than what they were already doing. 

Michael admits that the communication skills he developed back in his football management days turned out really helpful in his new role, especially charisma. When selling to executives, believing in what you're selling and the charisma that you can transmit to the customer is really important. According to Michael, that's something that gets you over the line. 

But also, communicating the value of what you’re offering to the customers is essential.

"Just being very clear about what this is, what it does, and how we can help them that is fundamentally what they care about. How can it help them be better leaders? How can it help them be better coaches? How can it help them be better operators? That is it."

Michael is a well-rounded salesperson today. But his transition from high-velocity sales to a more consultative approach and tackling complex deals required building certain skills. The top three are: 

• How to ask very deep questions to get to the real pain?
• How to go higher, wider in an organization?
• How to go from “I'm selling to you” to “I'm selling with you”?

These are the three skills you have to master when going from high-velocity, transactional to more complex, enterprise sales.

Building connections with different buyer personas

According to Michael, his team at Clari drives a really rigorous process around multi-threading. They know who their buyers are. They know what their pains are. They know what buyers care about. So starting very early in the cycle, they are already mapping out who they need to speak to. But it wasn’t always like that.

In his early days at Clari, it was mostly sales ops who they were speaking to most of the time. Which seemed reasonable because those people drive all the tech stack at any organization. However, they didn't really get any deals until they switched their focus to sales leaders — VP of Sales, Director of Sales, CRO, Chief Customer Officer, etc.

Once you map that out and know what your buyers all care about, then it’s just a matter of outreach. But how do you put together an outreach campaign or outreach plan to actually touch each and every single one of those personas? 

Michael shares that at Clari they are really successful in multi-threading. They build a connection with their target accounts by activating their leaders, their C-suite, and their board members at Clari.

That might involve writing notes for their VP to send to another VP. They would get their VPs connected to the VPs at the target account, they get their CRO connected to the CRO, and their CEO — to the CEO of that company.

Yet, to succeed with this strategy, you need a very clear idea of what leaders are looking for and what they are interested in. According to Michael, this includes:

• What's not working? 
• What's stopping growth? 
• Why they're losing deals? 
• How to get the B players to become A players?

Coaching and leadership in sales

Just recently, Michael saw a poll in one of the sales communities. The results shocked him — about 80 to 90% of the members responded that they don't get any coaching from their leaders. While it’s not the case for Michael himself, he considers that it might be because the VPs or Directors of Sales are busy with more strategic stuff. Yet, he argues that the fundamental first responsibility of a leader is coaching.

A leader who is willing to turn their B players into A players but won’t do the coaching is living in a dreamland. If they just want to get into the dashboards and fancy reports, for Michael, that's not leading.

So you have to lead by example, show them how they're doing things, the gaps that they could fill, and teach them how to do things better and more efficiently. And then they can see the results from it and then you can pat them on the back when they get the results from it. That's what leadership looks to Michael. 

Yet, this doesn’t mean that leaders shouldn’t use data at all. It can also help you turn your B players into A players by allowing you to see through loads of tools out there that give you analytics around a particular performer. 

"For example, tools like Clary Copilot, or Gong, or Mojo. These tools show you what your reps are doing well and what they're not doing so well. And you can tap into what they're not doing well and make it better and tweak it."

A leader who has that conversational intelligence inside there to identify some patterns, e.g., when the reps are talking too much or when they've not asked enough questions, they lose a customer. These are the insights you can use to coach.

Yet, even with the right tools and insights at hand, it's a very difficult task to coach people, to grow people. Your priorities might go somewhere where you feel more comfortable. So some “leaders” just don't want to get their hands dirty and do the hard work of actually understanding what are the common missteps of their reps, and how can they improve on them.

Sales enablement and playbooks in complex deals

According to Michael, sales leaders today are looking to get even more predictability around key deals that they're working on. That is super-important, especially now that there are high growth targets. 

To do that, tools like Flowla are helpful because they give leaders true insights and true predictability around what's really happening in a deal, where you're at versus what the sales reps might tell you. They are giving the true visibility around how engaged the buying committee is with your content, and how engaged they are with the rep. 

So Michael predicts that sales enablement tools like Flowla are going to enjoy more success simply because there is a need for more predictability in the sales cycle.

Another important part of sales enablement is compliance with playbooks. In enterprise sales, you have to have some guardrails around what you need to do to win the deal. So having proven playbooks, especially for new reps, is really important for them to see what's working, how they can emulate and how can they see success in a repeatable way. That's why playbooks are important. 

"At the end of the day, fundamentally the most important thing to a CEO is revenue. Revenue comes from your customers. So whatever you're doing in enablement, in leadership, if it's not tying into how to win deals more predictably, quicker, with more velocity, like, I don't know what you're doing."

As a leader, regardless of the actual title, it all boils down to what you are doing to affect deals and how you are helping your team win more deals. That is your mandate, your first responsibility — to affect the bottom line revenue. Not rolling out some training that is not going to impact it directly.

Skills, tools, and strategies to close complex deals

For Michael, a complex deal is when you have to navigate through loads of different stakeholders, you have to navigate through organizational politics, create a champion out of nothing, and essentially get the buy-in from the C-suite. Those four things make a complex deal.

So the first skill a junior rep should develop is relationship building. Michael considers it impossible to close a complex deal without having someone to partner with in the organization. If you don't have a champion who is willing to collaborate with you, learn from you, get guidance from you, and then expose you to their world, it's not going to happen. You won’t be able to close complex deals.

The second one is learning how to understand your customer's business, their strategic initiatives, how the solution they're selling ties into that, and how they're going to deliver ROI. Learning how to build really good business cases is also a skill that you have to develop in complex selling.

Those are the skills that can be developed, but there are also the basics like care, curiosity, and empathy you have to have. Because if you don't genuinely care about somebody else's issues and problems you won't go very far because you'll be bored. 

You should be in sales if you have that curiosity, the desire to learn more about people, learn more about customers' pain points, and what they care about. To be in sales, a person needs to be charismatic, good at communicating, at getting along with people. 

"If you're a magnet, if people would like to be around you, learn from you, and talk to you, you should definitely be in sales. Cause you have something that not many people have, which is the power of influence. You can influence people really well."

Michael’s go-to strategy for sealing a deal is to get a champion on text. It works for him every time — once he gets the champion on text, he closes the deal.

Key takeaways

• When selling to executives, believing in what you're selling and the charisma that you can transmit to the customer is really important.
• To succeed with multithreading, you need a very clear idea of what leaders are looking for and what they are interested in.
• A leader has to lead by example, show your reps how they're doing things, the gaps that they could fill, and teach them how to do things better and more efficiently.
• Sales leaders today are looking to get even more predictability around key deals that they're working on, which makes sales enablement tools like Flowla really important.
• The most important skills a sales rep should have for complex sales are relationship building, understanding your customer's business, and building really good business cases.

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