How to Scale Enterprise Sales Within Your Startup

Rob Crnkovic (Co-Founder & CRO, CapIntel), Vitaly Pecherskiy (Co-Founder & COO, StackAdapt)

SAAS NORTH NOW #88

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Hello to Canada’s SaaS Community,

Enterprise clients can change the trajectory of a startup, taking revenue, brand credibility, and growth to a whole new level—but how do you get your foot in the door of the enterprise world in the first place? We talked to Rob Crnkovic, the Co-Founder and CRO of CapIntel, and Vitaly Pecherskiy, the Co-Founder and COO of StackAdapt, about how they managed to break through.

Key takeaways:

  • Be specific: Start by getting clear on your target customer and their problems to identify an opportunity for a software solution.
  • Identify internal champions. Your first enterprise deals will likely be driven by motivated individuals who understand your product’s potential and will advocate for it within their organizations.
  • Be prepared to back up your pitch with a great trial and onboarding experience—a sales presentation alone won’t cut it.

Dave Tyldesley

Co-Founder/Producer, SAAS NORTH Conference Editor, SAAS NORTH NOW

1. Find an Opportunity

Working within the context of an enterprise calls for different software solutions, so it’s important to have a clear understanding of your target buyer and their problems. “Everybody’s running their own destiny or own company, and [an enterprise deal is] only going to happen if there’s value for them,” said Vitaly.

For Rob, this meant seeing a gap in technology within the wealth management industry. He and his co-founders noticed that while financial advisors leveraged a lot of technology to do their work, and customers interacted with a lot of financial marketing, there was nothing advisors could use to demonstrate to their clients the value of a portfolio in a way that they could easily understand. That’s when they decided to start CapIntel.

2. Build the Product

Although he’s a CRO, Rob works closely with the product team to make sure the product is aligned with the needs of its customers. He identifies three key features of a solid enterprise product:

  1. Scalability: Large enterprises have multiple departments comprising a range of roles, and while they might use the same software, they have different needs. Rob advises building a single platform with features that address core use cases.
  2. Configurability: Products should be adaptable and configurable to user needs, and ideally allow users to customize things themselves to avoid costly and time-consuming custom deployments.
  3. Connectivity: Software needs to work with the legacy infrastructure and tech stack of an enterprise company and take API connection into consideration. At CapIntel, they focus on systems that their target customers have in common to avoid API scope creep, and for more niche applications, they offer an API toolkit for the customer’s team to work with.

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3. Identify a Champion

Rob emphasizes that selling into enterprise companies isn’t just about having a good product. It’s about balancing enterprise-ready products with a supporting go-to-market strategy. To get the attention of decision makers and executives in enterprises, Rob said new startups need to demonstrate a point of view from the market, executive strategy, and individual customer perspectives. This will help capture attention (and hopefully passion) from individuals that can become champions for the product internally.

Vitaly has another approach to identifying potential customers: look for buyers who are willing to take a risk. “There’s always people that will take a leap of faith,” he said. “There are always organizations that are a little bit more nimble that you know where you can get that foothold.”

To find them, Vitaly said you’ll need to “just grind it out” to some degree, but you can also look for tell-tale signs, like whether they’ve bought from startups before, if they have an internal innovation team, or if they are supporters or sponsors of startup communities. Once you’ve narrowed the pool a bit, he recommends talking to as many people as you can to find your champion. “In the early days, sell like crazy into as many customers as you can,” said Vitaly. “And you will find those people.”

4. Demonstrate Value

Once this “champion” is identified, you need to be able to clearly articulate a value proposition that resonates with them; Rob says that this message is usually about cutting costs or increasing revenue.

Another tactic that Vitaly recommends is offering a structured trial, rather than just asking for a sale or a contract. It’s important to show that you can solve the customer’s problem, demonstrate how you measure success, and prove some value. “You need to deliver real value, not just a sales pitch,” said Vitaly.

5. Back It Up & Deliver

There are lots of ways to demonstrate credibility to your customer, and showing that you can think big-picture is one of them. Rob said CapIntel starts with executive-level concerns and perspectives, informed by their champion. From there they drill down to the level of the individual user, communicating how their solution helps advisors close clients. After that, they circle back to the executive arena, connecting individual performance to higher-level pain points and goals.

Another important angle is accountability. During the sales process, Vitaly emphasizes the importance of explaining how you’ll support the company through the trial and ultimately onboarding if they decide to buy. And then, of course, you have to follow through.

“We see this time and time again; we get excited about something, but the vendor doesn’t hold us accountable to onboarding and measuring value,” said Vitaly. “Six months later, people stop using it and we never renew. And that’s a waste of time for everybody.”


SAAS NORTH is THE Canadian hub for rapidly-scaling SaaS founders and their teams. Learn, network, and grow with Canada’s largest in-person SaaS community at SAAS NORTH.

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Hello to Canada’s SaaS Community,

Enterprise clients can change the trajectory of a startup, taking revenue, brand credibility, and growth to a whole new level—but how do you get your foot in the door of the enterprise world in the first place? We talked to Rob Crnkovic, the Co-Founder and CRO of CapIntel, and Vitaly Pecherskiy, the Co-Founder and COO of StackAdapt, about how they managed to break through.

Key takeaways:

  • Be specific: Start by getting clear on your target customer and their problems to identify an opportunity for a software solution.
  • Identify internal champions. Your first enterprise deals will likely be driven by motivated individuals who understand your product’s potential and will advocate for it within their organizations.
  • Be prepared to back up your pitch with a great trial and onboarding experience—a sales presentation alone won’t cut it.

1. Find an Opportunity

Working within the context of an enterprise calls for different software solutions, so it’s important to have a clear understanding of your target buyer and their problems. “Everybody’s running their own destiny or own company, and [an enterprise deal is] only going to happen if there’s value for them,” said Vitaly.

For Rob, this meant seeing a gap in technology within the wealth management industry. He and his co-founders noticed that while financial advisors leveraged a lot of technology to do their work, and customers interacted with a lot of financial marketing, there was nothing advisors could use to demonstrate to their clients the value of a portfolio in a way that they could easily understand. That’s when they decided to start CapIntel.

2. Build the Product

Although he's a CRO, Rob works closely with the product team to make sure the product is aligned with the needs of its customers. He identifies three key features of a solid enterprise product:

  1. Scalability: Large enterprises have multiple departments comprising a range of roles, and while they might use the same software, they have different needs. Rob advises building a single platform with features that address core use cases.
  2. Configurability: Products should be adaptable and configurable to user needs, and ideally allow users to customize things themselves to avoid costly and time-consuming custom deployments.
  3. Connectivity: Software needs to work with the legacy infrastructure and tech stack of an enterprise company and take API connection into consideration. At CapIntel, they focus on systems that their target customers have in common to avoid API scope creep, and for more niche applications, they offer an API toolkit for the customer’s team to work with.

3. Identify a Champion

Rob emphasizes that selling into enterprise companies isn’t just about having a good product. It’s about balancing enterprise-ready products with a supporting go-to-market strategy. To get the attention of decision makers and executives in enterprises, Rob said new startups need to demonstrate a point of view from the market, executive strategy, and individual customer perspectives. This will help capture attention (and hopefully passion) from individuals that can become champions for the product internally.

Vitaly has another approach to identifying potential customers: look for buyers who are willing to take a risk. “There’s always people that will take a leap of faith,” he said. “There are always organizations that are a little bit more nimble that you know where you can get that foothold.”

To find them, Vitaly said you’ll need to “just grind it out” to some degree, but you can also look for tell-tale signs, like whether they’ve bought from startups before, if they have an internal innovation team, or if they are supporters or sponsors of startup communities. Once you’ve narrowed the pool a bit, he recommends talking to as many people as you can to find your champion. “In the early days, sell like crazy into as many customers as you can,” said Vitaly. “And you will find those people.”

4. Demonstrate Value

Once this “champion” is identified, you need to be able to clearly articulate a value proposition that resonates with them; Rob says that this message is usually about cutting costs or increasing revenue.

Another tactic that Vitaly recommends is offering a structured trial, rather than just asking for a sale or a contract. It’s important to show that you can solve the customer’s problem, demonstrate how you measure success, and prove some value. “You need to deliver real value, not just a sales pitch,” said Vitaly.

5. Back It Up & Deliver

There are lots of ways to demonstrate credibility to your customer, and showing that you can think big-picture is one of them. Rob said CapIntel starts with executive-level concerns and perspectives, informed by their champion. From there they drill down to the level of the individual user, communicating how their solution helps advisors close clients. After that, they circle back to the executive arena, connecting individual performance to higher-level pain points and goals.

Another important angle is accountability. During the sales process, Vitaly emphasizes the importance of explaining how you’ll support the company through the trial and ultimately onboarding if they decide to buy. And then, of course, you have to follow through.

“We see this time and time again; we get excited about something, but the vendor doesn’t hold us accountable to onboarding and measuring value,” said Vitaly. “Six months later, people stop using it and we never renew. And that’s a waste of time for everybody.”


SAAS NORTH is THE Canadian hub for rapidly-scaling SaaS founders and their teams. Learn, network, and grow with Canada’s largest in-person SaaS community at SAAS NORTH.