Chase talks about what it takes to sell B2B SaaS in 2023: Value, Curiosity, Financial Acumen, Leading by Example, and AI

published on 16 May 2023
In conversation with Chase Tarkenton, Executive SaaS Revenue Leader and Vice President, North America Sales at Uniphore
In conversation with Chase Tarkenton, Executive SaaS Revenue Leader and Vice President, North America Sales at Uniphore

In this discussion, Chase advises B2B SaaS sales leaders to:

  • Put a spotlight on the value
  • Promote and hire for curiosity
  • Teach financial acumen, involve your CFO
  • Lead by example, show them how it is done
  • Drive change internally, like you sell externally
  • Leverage AI

Put a spotlight on the value

Customers grow numb to their pain. You need to spotlight it. Your conversations have to be predicated on what your customer is trying to solve for. 

And that's not enough. We have to take it a step further and say, ‘Oh, by the way, how do we make sure that your CFO sees value in what we're positioning from a solution standpoint?’

The higher you are selling into the organization, the more it needs to be a data-based, financial conversation.  If someone comes to the table and says, "Let me show you how I've helped X amount of my clients reach 120% of their annual growth target and oh by the way, 80% of the reps were able to hit their number." You have got my attention. 

It's quantifiable. It's not subjective. It's not a vanity pain that we're solving at that point. And I think this is the broader narrative for anyone out there, regardless of whether you're selling software or what have you.

Your proposal is going to go to the CFO in 2023. Guaranteed. If you haven't done your due diligence to capture financial impact, if you haven't found a champion within the organization, that can say, ‘Hey, Sumit, this is how my finance team or CFO is going to look at this particular proposal. And here are the success criteria financially. Or here's how they evaluate cost’. If you haven't gotten to that level of granularity, you're going to have a really hard time in this economy.

Promote and Hire for curiosity

The best sellers that I've ever worked with, they are genuinely curious about their customer’s business. 

They don't go in and just start talking about all the capabilities of what they do, or ‘let me tell you about my company’. They spend an enormous amount of time, just getting the person on the other side of the table or the video, to educate themselves on the business. 

As a revenue leader, you have to promote that behavior and make sure that you are hiring for that.  I don't know that you can really make someone be curious about someone else. So you definitely have to make sure you make curiosity a core hiring trait. 

Teach financial acumen, involve your CFO

Train your folks on financial acumen. Most salespeople that I've encountered in my career don't know how to read a balance sheet. 

In a previous economic downturn, I was leading the go-to-market for a global SaaS company. We knew we needed a better financial story to close business, so we educated our sales team on financial statements and brought in the CFO to speak at our sales kickoff.

And I think he may have been a little nervous to probably get peppered with questions from sales. I think sales reps were a little intimidated too, to be talking to the CFO. You almost had opposing forces talking to one another. But by the end of it, I think everyone walked away with a better understanding of how those audiences work.

We immediately implemented a process to understand our clients' financial scorecards. This involved doing research on the front end, asking good questions during discovery, and aligning some of those questions with the CFO's success criteria. This was a great way to find out if the individual we were speaking with was someone who could ultimately get our deal across the finish line. If they could answer our questions, we knew we were talking to a seasoned executive who could help us get the deal done. If they couldn't answer our questions, we still had some work to do.

The hack is to learn from your own CFO. They make decisions every day that impact the success of your company. Ask them questions about their role, the company's finances, and how you can be more successful in your own work. You'll be glad you did.

Lead by example, show them how it is done

When you have a sales organization with a variety of personalities and backgrounds, it's important to implement formal training that sets a common baseline. E-learning modules are a great way to do this, as they allow you to track everyone's progress and ensure that everyone is learning the same material. Third-party trainers can also be a valuable resource, as they can bring in fresh perspectives and new methodologies.

But, what really moves the needle is that as a sales leader you are committed to the methodology you are teaching your team. You need to truly embrace it and make it a part of your own selling ethos if you want the team to do it. 

Your best sellers are most likely going to come to you and say, "Hey, I hear you and I recognize the importance of this methodology, but I'm just not good at it. Can you show me how it's done? I'll learn anything if it helps me hit my number."

When that happens, you need to be ready to step up and show them how it's done. You need to lead by example. If you want your team to do something, you need to be willing to do it yourself.

One of the best ways to do this is to let your team see how a customer executive reacts when you speak about your solution from a financial perspective. When they see the positive reaction, they'll be more likely to adopt the methodology themselves.

In my experience, this is an undeniably effective way to get your team on board with a new methodology. I recognize it is hard for sales leaders because if you are not intentional about being customer-facing as an executive, it's easy to lose touch with customers as you move up the corporate ladder. You can fall into the trap of being more internally focused. And less externally focused. You need to adapt and learn quickly. If you do, you will win. 

There is more. Bring folks to the table. One of the best things I've seen in my career is when a CEO or executive leader brings a sales rep to their customer meeting. The sales rep often walks away saying, "Wow, that was a completely different conversation than I've ever had."

Let them get a feel for how executives speak to one another. What are the questions that come up? In doing so, you are teaching your team how to be executive-centric. And that's just one other way to really level up and beat the competition. Especially in 2023. 

Drive change internally, like you sell externally

I've never been a part of an organization where salespeople were excited about a new process. Even if the process is good for them. Sales reps would say, "Hey, but by the way, I've got a number to hit right. And every time I spend an hour doing something internal, that potentially takes me away from a customer-facing activity that could drive sales and maybe drive it in this month or this quarter or this year."

There's always going to be resistance. But if you want to find the right balance that helps the organization, have a conversation on the front end between the stakeholders. 

I was once part of a team that was trying to improve our discounting controls. We were giving out too many discounts, and it was getting out of control. We needed to implement a process to control discounts, but we didn't want to slow down the sales team. 

Salespeople saw the new process as an unnecessary burden that will slow them down. Rev ops saw the new process as a way to align with the CFO and ensure that we were giving out discounts in a responsible way. Both parties were right.

There was so much friction. They were so upset at one another. So we brought folks together. And when we went through that simple process of explaining and understanding, everyone walked away with a better grasp of, ‘Oh, now I get it’. Context is everything. 

It's ironic that we often use a different playbook when problem-solving with our internal customers than we do with external customers. When we're working with external customers, we take the time to understand their pain, perform discovery, and work through the different stakeholders. We ultimately align on a path forward that solves their issue. We need to do the same with internal customers -- understand their success criteria, what it means to them, who they have to go to for approvals, or why they're resistant to change.

The playbook is simple. Be curious, open to discussion, and helpful. Align on a path forward, then problem-solve and execute.

Leverage AI

AI is super exciting right now. Overwhelmingly, when I talk to customers and clients at some of the biggest companies, the biggest potential for AI is to augment humans. Sure, there's cost containment. I don't have to hire as many people, but I can actually do more work. I can cover more ground. My sales force can get to more customers, even though I haven't had to increase my overhead significantly to get there. 

Within sales, I'm excited about how AI is being implemented for use cases like forecasting, quoting, and proposal generation. Reps in all industries spend far too much time creating quotes, and they have to go through a lot of different layers within the organization to create something that should be pretty easy to do. And many companies create proposals that may not be as easy to understand.  AI can help. 

I encourage people out there thinking about this. How do you augment your people? Get that force multiplier. I think in the long run it's going to create tremendous economic prosperity for people, provided we're responsible with it along the way.

About Chase Tarkenton: For nearly twenty years, Chase has held various roles focused on expanding revenue and market share. Before his current role heading North America Sales segments for Uniphore, Chase served as EVP of Americas Sales, Alliances and Consulting Services at Eleveo, where he spent over 10 years establishing himself as a leader focused on outcomes, not soundbites. He's advised Techstars, invested in companies like, and serves on the board of Shelters to Shutters. He believes in fostering a DEI culture and centering personnel on long-term value creation.

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