In this week’s episode of CRO Confidential, host Sam Blond wraps up the founder-led sales series with one of the most accomplished sales leaders in the world, Brendon Cassidy. 

Cassidy was Blond’s VP of Sales at Echosign and, before that, was one of the first sales leaders at LinkedIn. Post-Echosign, he was the first sales leader at Talkdesk, valued at $10+B. Cassidy is now a co-founder at CoSell, a.k.a. the relationship platform designed to organize your intro efforts. 

The point of CRO Confidential is to help startups acquire customers, and Cassidy provides a unique perspective on founder-led sales as a current founder and highly talented sales leader. 

So what secrets has Cassidy learned over the past decades of building businesses and acquiring customers? 

Let’s find out. 

Toss Out The Cold Outreach Playbook

Not everyone agrees with this idea, but Cassidy believes that the cold outreach playbook of spamming the market with quasi-personalized messages is waning, and response rates are decreasing. 

Everyone’s been prospected to, so there has to be a different way to make mutually beneficial connections with people of influence. 

Of course, you shouldn’t throw out cold outreach completely, but implementing more effective strategies in addition to effective outbound is always a good thing. 

And that’s why CoSell was created, to increase the chance of startups making it by helping GTM teams tap into and connect with people who can help them take the most strategic path to customers with credibility and warmth — because 90% of those startups won’t survive. 

Leverage Personal Networks

Not everyone knows the Brendon Cassidy, Sam Blond, or Jason Lemkin’s of the world — people with expansive and powerful networks within a target market. 

But if you can leverage your network and the networks of people around you, it will generate a lot more opportunities than the spray-and-pray method of outbound. 

CoSell aims to unlock the connectors or gatekeepers of the world in a way that makes it a win for them and the early-stage founders looking for real support. 

Early-stage startups who aren’t yet household names need to find a way to leverage warm intros to companies instead of cold-emailing sales leaders.  

Creative Ways To Make Outbound Work For You

When you implement any kind of GTM strategy, you want it to work. No one wants to throw money at something that falls flat. That’s why you need to get crafty and come up with unique and meaningful ways to reach people. 

Some successful campaign ideas Sam and Brendon have seen or implemented include the following: 

  • The Champagne Campaign. At Brex, Sam’s team sent champagne bottles and a handwritten note of congrats on recent fundraisers to different organizations. The campaign had a 75% reply rate and a 75% conversion rate.
  • Launch Day billboards. On the day Brex launched, they put billboards up all over San Francisco. They were deliberate about reaching out to companies headquartered in downtown SF specifically because they knew who Brex was. They took advantage of marketing and brand tailwinds to increase their probability of success.
  • A company in the legal tech space had yet to respond to traditional digital outreach and cold calling. The solution: Drop off donuts and swag inside law firms to drive engagement and visibility. And it worked!
  • At Echosign, Sam closed Aetna and created a press release about the millions of pieces of paper they saved each month. They took that case study to BCBS, Cigna, and others and won them all. 


Each of these examples has something in common: community. 

When someone opens a bottle of champagne or chows down on donuts at work, they will ask, “Who sent this?” They likely share the goodies as a team to celebrate, and they’ll remember who brought everyone together. 

In the case of Aetna, they’re creating a sense of desire for community. “I want to save a million pieces of paper each month too!” And everyone jumps on the bandwagon. 

This is much different than someone sending a LinkedIn message saying, “I’ll give you a Starbucks gift card if you take a call with me.”

If your outbound is effective, your customers will come to you without you needing to bribe them outright. 

Allow Existing Customers to Get New Customers

You have to pay a price for getting new customers or connecting with the gatekeepers who will help you get new customers. 

That price isn’t always monetary, although financial incentives are pretty compelling. But everyone needs to feel like they’re winning. 

For example, while Cassidy advised Gong in the early days, he, the founder and CEO, two VP of Sales, and a couple of investors had an incredibly strong network in the space. They didn’t need much help getting those first 100 customers. 

Those first 100 customers set the tone for the next 1000 because they were raving fans and credible sources for their own networks. 

If you’re cold-calling, you don’t have the same level of loyalty that you have with someone you know and trust. 

But if you don’t have a robust network to start, CoSell provides it for you because these super-connectors become paid advisors who use their influence to get you warm intros into your target market. 

If you want more customers, create raving fans in your original set of customers. Encourage and incentivize them to tap their own networks to continue growing your business. 

The Takeaway

All three founders in this founder-led sales series have referenced three of the same things each is doing to acquire new customers. While the term “playbook” needs to be taken loosely, there’s undoubtedly a trend here. 

Each founder suggests early-stage startups to: 

  1. Leverage advisors and personal networks to acquire their first set of customers. 
  2. Leverage existing customers to get that next set of customers. 
  3. Constantly throw ideas against the wall to see what sticks. 

Brendon’s final advice for early-stage startups (and all organizations) is to have a compelling answer to the problem you’re solving. 

Be able to share that answer in one sentence. If you can’t, pause, step back, and figure it out.

One of the reasons so many startups fail is because they don’t know what problem they’re solving for. The market won’t come to you if it doesn’t know how you can solve its problems. Once you’ve figured it out, you’ll be well on your way to acquiring new customers. 

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