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SAAS NORTH NOW Blog

How To Break The Startup Chicken-and-Egg Problem Of Enterprise Sales

Vitaly Pecherskiy, Co-founder & COO, StackAdapt

SAAS NORTH NOW #59

Hello to Canada’s SaaS Community,

If you want enterprise customers, you need to understand how you help them grow. Yet you often can’t know all the details until you get a few customers. Speaking with SAAS NORTH after his conference talk, Vitaly Pecherskiy, co-founder and COO of StackAdapt, explained how he broke through this chicken-and-egg problem—and how other founders can too.

Key takeaways:

  • The best way to source potential enterprise deals is by looking for buyers who have already signaled they are willing to take a risk on a young startup.
  • Your product needs to be mature enough to support enterprise scale.
  • Your sales approach needs to prioritize demonstrating value rather than pitching a vision.

Dave Tyldesley

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

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You can’t win enterprise deals without experience in the space… but you can’t get experience until you win a couple of deals.

Breaking through this chicken-and-egg problem is essential to grow from selling to anyone into selling to enterprise customers. It’s something Vitaly Pecherskiy successfully accomplished as he scaled StackAdapt to over 1,000 employees and works with some of the world’s largest organizations.

Speaking with SAAS NORTH after his conference talk, Vitaly shared how StackAdapt broke through the enterprise sales wall—and how you can, too.

Who is willing to take a risk?

Vitaly said the solution to breaking into enterprise sales for a budding startup is two-fold and starts with your buyer. Rather than chasing the biggest whales you can possibly imagine, his advice is to look for buyers willing to take a risk.

“There’s always people that will take a leap of faith,” said Vitaly. “There’s always organizations that are a little bit more nimble that you know where you can get that foothold.”

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This usually comes in one of two forms:

  1. Organizations that are geared for more innovative action, or;
  2. Single leaders within traditional organizations who are willing to take a risk.

When it comes to finding these buyers, Vitaly said you’ll need to “just grind it out” to some degree, but also look for tell-tale markers such as if they’ve purchased from startups before, if they have an internal innovation team, or if they are supporters or sponsors of startup communities.

Vitaly’s second piece of advice on the buyer side is to find a champion—this has to be someone with influence (and preferably direct access to budget) internally who sees value in your solution. And the only way to cultivate champions is by talking to many people over time.

“In the early days, sell like crazy into as many customers as you can,” said Vitaly. “And you will find those people.”

Your sales process needs maturity

Champions and innovative, risk-taking buyers alone won’t secure you any deals. At the end of the day, you need the product and process to make it happen.

A mature product doesn’t necessarily mean having every feature or being an all-in-one platform. To Vitaly, what it really means is you can deliver demonstrable value to an enterprise. Your business process, then, needs to support and enable that value delivery.

Here are a few go-to-market features Vitaly said were crucial for StackAdapt’s growth in enterprise sales—and what he recommends other founders build alongside their product maturity.

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Structured trials: Not just asking for a sale or contract, but a trial where you can show you 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.

Hand-holding and accountability: Part of your sales process needs to be explaining how you’ll support the company through the trial and ultimately onboarding if they buy. Then 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.”

Basic procurement, legal, and compliance knowledge: Having a general understanding of what back-office functions need will help make the sales process smoother. It’s not an upfront requirement, since these steps are rote expectations in enterprise sales, but you need to know they are coming. However, if you can anticipate major needs–for instance, security issues when selling into banks–you can leverage that to build trust with your buyer.

Going beyond product-led growth (PLG): If your startup is focused on PLG, Vitaly cautioned that you can get some great initial traction, but you need to back that up with a different enterprise sales plan.

“You want to essentially have a SWAT team go as soon as possible to explain to the leaders in the organization why this product is important and help them get on your side,” said Vitaly.

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Manifest your own destiny

As a founder, it can feel demoralizing to lose sales or not even be taken seriously. But within that rejection is a gem of truth: everyone is in it for themselves and “nobody’s here to rescue you.”

While this may sound hostile, it can be a blessing. With everyone doing their own thing, you have a way in—if you can communicate how you deliver value for someone, you have a much stronger chance of closing the deal. It’s both that straightforward and that difficult.

“Everybody’s running their own destiny or own company, and it’s only going to happen if there’s value for them,” said Vitaly.

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Hello to Canada’s SaaS Community,

If you want enterprise customers, you need to understand how you help them grow. Yet you often can’t know all the details until you get a few customers. Speaking with SAAS NORTH after his conference talk, Vitaly Pecherskiy, co-founder and COO of StackAdapt, explained how he broke through this chicken-and-egg problem—and how other founders can too.

Key takeaways:

  • The best way to source potential enterprise deals is by looking for buyers who have already signaled they are willing to take a risk on a young startup.
  • Your product needs to be mature enough to support enterprise scale.
  • Your sales approach needs to prioritize demonstrating value rather than pitching a vision.

You can’t win enterprise deals without experience in the space… but you can’t get experience until you win a couple of deals.

Breaking through this chicken-and-egg problem is essential to grow from selling to anyone into selling to enterprise customers. It’s something Vitaly Pecherskiy successfully accomplished as he scaled StackAdapt to over 1,000 employees and works with some of the world’s largest organizations.

Speaking with SAAS NORTH after his conference talk, Vitaly shared how StackAdapt broke through the enterprise sales wall—and how you can, too.

Who is willing to take a risk?

Vitaly said the solution to breaking into enterprise sales for a budding startup is two-fold and starts with your buyer. Rather than chasing the biggest whales you can possibly imagine, his advice is to look for buyers willing to take a risk.

“There's always people that will take a leap of faith,” said Vitaly. “There's always organizations that are a little bit more nimble that you know where you can get that foothold.”

This usually comes in one of two forms:

  1. Organizations that are geared for more innovative action, or;
  2. Single leaders within traditional organizations who are willing to take a risk.

When it comes to finding these buyers, Vitaly said you’ll need to “just grind it out” to some degree, but also look for tell-tale markers such as if they’ve purchased from startups before, if they have an internal innovation team, or if they are supporters or sponsors of startup communities.

Vitaly’s second piece of advice on the buyer side is to find a champion—this has to be someone with influence (and preferably direct access to budget) internally who sees value in your solution. And the only way to cultivate champions is by talking to many people over time.

“In the early days, sell like crazy into as many customers as you can,” said Vitaly. “And you will find those people.”

Your sales process needs maturity

Champions and innovative, risk-taking buyers alone won’t secure you any deals. At the end of the day, you need the product and process to make it happen.

A mature product doesn’t necessarily mean having every feature or being an all-in-one platform. To Vitaly, what it really means is you can deliver demonstrable value to an enterprise. Your business process, then, needs to support and enable that value delivery.

Here are a few go-to-market features Vitaly said were crucial for StackAdapt’s growth in enterprise sales—and what he recommends other founders build alongside their product maturity.

Structured trials: Not just asking for a sale or contract, but a trial where you can show you 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.

Hand-holding and accountability: Part of your sales process needs to be explaining how you’ll support the company through the trial and ultimately onboarding if they buy. Then 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.”

Basic procurement, legal, and compliance knowledge: Having a general understanding of what back-office functions need will help make the sales process smoother. It’s not an upfront requirement, since these steps are rote expectations in enterprise sales, but you need to know they are coming. However, if you can anticipate major needs–for instance, security issues when selling into banks–you can leverage that to build trust with your buyer.

Going beyond product-led growth (PLG): If your startup is focused on PLG, Vitaly cautioned that you can get some great initial traction, but you need to back that up with a different enterprise sales plan.

“You want to essentially have a SWAT team go as soon as possible to explain to the leaders in the organization why this product is important and help them get on your side,” said Vitaly.

Manifest your own destiny

As a founder, it can feel demoralizing to lose sales or not even be taken seriously. But within that rejection is a gem of truth: everyone is in it for themselves and “nobody’s here to rescue you.”

While this may sound hostile, it can be a blessing. With everyone doing their own thing, you have a way in—if you can communicate how you deliver value for someone, you have a much stronger chance of closing the deal. It’s both that straightforward and that difficult.

“Everybody's running their own destiny or own company, and it's only going to happen if there's value for them,” said Vitaly.