Hiring for sales in a product-led world

Main illustration: Alexandra Bond

Founders make natural salespeople. So much of what they do, particularly fundraising, is selling. They’re the first and best salesperson your company will ever have.

But even if you have a great product, there will come a point where you simply need to build out a sales function. This can be a terrifying thought to anyone whose image of sales resembles Silicon Valley stereotypes.

Potentially the greatest culture clash a startup will ever face is the day they bring in their first sales team. But if you scale this function with intention, a sales org will enrich your company’s existing culture, help you build better product, and sell it too.

Getting the right team is the hardest part. As VP of Sales at Intercom, I lead a 50-person team that aspires to be both world class and culture additive, and plan to continue building out the best team possible for Intercom. Here’s how we thought through what was most important to us in the early days of team formation.

Discuss your company’s non-negotiables

A healthy discussion for founders to have with their early sales leaders is to identify each other’s non-negotiables. This is a discussion of values and ways of working. There are two questions in particular that should be addressed:

What absolutely must not change about the company’s culture when you bring in a sales team? For us, it was:

  • We’re product-led – At Intercom we’re product-led, rather than sales or marketing-led. We value a positive customer experience above all else. As it pertains to sales it means we will never subject all our customers to crappy features just because the highest bidder wants them.
  • We’re personal – Another non-negotiable is keeping communication with leads personal and respectful, a testament to our mission of making business personal. We dogfood our own products. We strive to make data-informed decisions about who, when and where to talk to a lead.
  • We value impact – We believe in a culture where people come to the office to focus and make an impact, and then go home at a reasonable hour. You may think this is an obvious one, but it’s not always true in practice. Lots of offices support a laissez-faire work ethic where people come and hang out for hours on end. Eoghan, our CEO, and I clicked when early on he said he never wanted us to own a ping pong table. It’s a small thing, but ping pong tables send the message that your office is an adult playground where you go to play and stay late.

Where can we bend to accommodate different work styles, personalities and traditions?

  • Volume – When I first came to Intercom the work environment was really quiet in order to allow people to focus. That’s great, but in sales we need to be able to talk comfortably out loud, bounce ideas off of each other, listen to each others’ calls. We create spaces to support this that don’t disrupt other teams.
  • Recognition – Another thing we’re exploring is how we externally motivate our sales people. I’m a big believer in positive reinforcement and the symbolic banging of the gong. We continue looking for ways to celebrate our team in a way that fits culturally. For example, we’re exploring technologies that would allow us to celebrate accomplishments in real time. We do a monthly global all hands and regional all hands even more frequently. We want to ensure there is a good platform to celebrate all the fantastic things going on in the business and share best practices.

The traits of product-led salespeople

Once you and your executive team are on the same page in terms of values, you can surround yourself with the right talent. Just like how Darragh has written about the traits he looks for in exceptional engineers, here’s what I value most when looking for great salespeople for Intercom.  

  • They respect product. In a product-led company this is really important. Salespeople don’t always need technical backgrounds to sell business software, but they certainly need to be passionate about the product and how it relates to the company’s mission and vision. They’re innately curious about how the product could evolve to delight users and they care deeply about customer success.At a product-led company you’re constantly looking at ways to better connect your go to market and R&D functions, and striving to be thoughtful in the types of customer insights you deliver.
    • They’re resilient. Sales people will get rejected time and time again and fail to win deals more often than not. You want people with a track record of resilience and grit. I always ask candidates:
      • When have you failed?
      • How did you pick yourself up and move forward?
      • What did you learn and how have you evolved as a result?

A good example response might be: “I really messed up a large customer acquisition deal that I was working on. My manager and I worked together to understand that I hadn’t actually done discovery at the right levels within the organization so I never had executive buy-in. I learned a ton from that. We actually came up with a plan to make sure that I’m getting in at the right level for these types of large, complex deals moving forward.”

Besides listening to their response, watch for non-verbal signs. Are they comfortable with, are they owning up to, their failures? Or are they dismissive, agitated, defensive?

    • They care about more than quotas. In sports, stacking your team with all-star players doesn’t always lead to a championship. Similarly in sales, hiring prima donna salespeople rarely leads to a great sales quarter. Great sales people care deeply about driving to cross their own personal quotas, but they care about the company too. How can you tell?
      • They go out of their way to deliver customer feedback to product teams.
      • They’re dedicated to protecting your non-negotiables.
      • They’re fired up to help the team create best practices and scalable processes.
      • They raise fellow salespeople along the way and instinctively understand the whole is greater than the sum of their parts.

None of those things will ever directly impact their quotas, but they’ll lead to a better customer experience and product and ultimately, these things are easier to sell. It’s a win-win.

    • They don’t solely rely on past playbooks. Your first sales hires have to be comfortable with ambiguity and happy to help create the playbook. This is absolutely critical because while some best practices from their previous experience might apply (like a solid discovery process), there are a lot of unknowns in the go to market process that have to be figured out for your specific company. Understanding what pitch resonates, how to speak to your specific buyer, what competitive differentiation is effective, etc, cannot simply be extrapolated from their previous role.

Look for folks who get excited to be part of the team that helps create the path forward for the next generation of sales people to come. One question I like to ask candidates is for an example where they improved a process or innovated in some way.

Value drives culture

Jason Fried once wrote, “You don’t create culture. Culture happens. It’s the byproduct of consistent behavior.” We can talk at length about what a sales culture should look like, but in the end, it’s a tapestry of the people you fight to hire, the values you uphold, the behaviors you celebrate. These values come first. 

Want to grow a world-class sales team? Industry leaders – LB Harvey, Alyssa Merwin and Richard Harris – explain how in this webinar.