Insights from category creators and the investors who believe in them.

Evolving Enterprise: Scaling the Go-To-Market Team

March 23, 2022

Once you define product-market fit, the next step is building a killer go-to-market team that can go out and sell your product to your target customers. But hiring a sales team that can execute on your vision is a huge challenge. 

To learn top strategies for finding, hiring, training, evaluating, and supporting the best sales team, we recently sat down with two enterprise sales experts: Abbie McBride, Chief Revenue Officer at WorkBoard, and Kevin Van Gundy, Chief Revenue Officer at Vercel

Watch the replay, or check out their advice on common questions from startup founders:

How do I transition from founder-led sales to hiring a sales leader?

Get the timing right. If you do this too early, you will have someone sitting around twiddling their thumbs; if you do it too late, you will miss out on important growth opportunities. Nail your product-market fit, then go hire a sales leader.

Make sure the first sales leader you hire is an evangelist. This person needs to bring your vision and perspective into the world, and then scale and translate that vision into impact and value for your business.

When onboarding your first sales leader, expect to spend 90 days just transmitting the company’s spirit into that person. Have this person do tons of meetings, meet customers, go on sales calls, and closely observe how the CEO talks about the product and the company’s ethos.

Understand that the first sales leader you hire may not be the one who leads the sales team two to three years later. As the company grows and changes, you’ll need to hire sales leaders with different skill sets.

Hire people who are curious, collaborative, creative, and competitive. These four Cs are the most important characteristics of a salesperson who will be excellent at both prospecting and execution.

How do you train remote sales teams?

Follow these six steps to successfully onboard and train remote workers on your sales team:

  1. Make onboarding as engaging as you can, even if it’s mostly online. Try a 30-day onboarding that provides general learning, tailored lessons, fun events, bonding exercises, feedback, customer stories, roleplays, and more. At the end of this, your new sales team members will share a common nomenclature, culture, and vision.
  2. Use learning management systems (LMS) tools. There are lots of great platforms that help train sales teams, offer sales enablement tools, and even let salespeople upload videos of themselves giving pitches to get feedback.
  3. Record sales calls, and then use them as training tools. Mentors can hold weekly coaching sessions with sales reps to review these recordings to assess what they did right and where they could improve.
  4. Go beyond Zoom and videos. Really good mentoring happens face-to-face or over the phone, because people feel more receptive when not staring at their own face on a screen. Zoom is a powerful tool; just don’t overdo it.
  5. Get junior sales people together with senior staff. Team members who are newer to the sales process need a lot of mentoring and support, and there’s no one better to help them than people who’ve already walked in their shoes.
  6. When all else fails, get people together in person. You can hold outdoor events if that’s what everyone feels most comfortable doing, but there is no substitute for learning in person from one another.

How do you measure a sales team's success?

Evaluate metrics that aren’t just about closing. For example:

  • Look at a person’s pipeline
  • Assess skills via roleplaying
  • Check completion of a sales enablement workshop 

If you want to measure one key metric, choose net dollar retention. That shows that a rep is not just good at closing deals but great at selling to customers who will stick around for the long haul. Look three, four, or five years out to see which reps have the highest net dollar retention over time.

Remember: Measure a rep’s progress on his or her own journey instead of comparing to others. Is this person continually getting better? If not, what tools and support can you offer?

When it comes to building a go-to-market sales team, what are some common mistakes?

Mistake #1: Waiting too long to hire a sales-op leader. This person designs the architecture of your entire sales process, so you need to hire as early as possible. Getting the structure of your sales organization right from the beginning is the highest priority.

Mistake #2: Not working closely with technical teams. Engineers create the product you sell, often bending over backwards to add the features you request. Customer success, developer relations, and professional service teams work with customers every day. Get to know them all—and appreciate their work.

Mistake #3: Going after big partnerships in the early days. It may seem exciting to sign a channel partnership, but the reality is that it’ll take a lot of your time and attention (and likely five full-time staffers) to manage the relationship. These partnerships are usually not accretive to early-stage startups.

Mistake #4: Trying to close perfectly structured deals early on. It’s better to close bespoke deals for your first 25-50 customers than to have no customers at all. And early customers provide invaluable feedback.

Get more tactical tips and actionable advice in our Evolving Enterprise series: