Celebrating Your Losses to Improve Your Sales Process

Seller's Journey Episode 5
Transparent sales process - working together
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Welcome back to the From Vendorship → Partnership podcast, Season 2: Seller’s Journey! 

This season, we’re talking to B2B sales leaders about their experience building winning processes, coaching & scaling teams, and partnering with customers.

Our guest this week is Kevin Nothnagel, VP of Sales at Clockwise!

Kevin is a multi-time sales and revenue leader with a wealth of sales and PLG knowledge from his time at Dropbox, Productboard, and now growing the team at Clockwise. He and Ross talk about building playbooks, celebrating your losses, and other sales teams they look up to.

Listen to the episode here, and get the highlights from our conversation below.

📕 Why is it important to build sales playbooks at startups?

Documenting your process and building your sales playbook is a critical – but challenging – step for startups, especially at the early stage.

“It’ll change as soon as you write it down,” says Kevin. “But the foundations you set today will grow with you and be useful 2-3 years in the future. It’s a worthwhile investment.”

Building and iterating on your playbook will help you answer questions like:

  • What outbound messaging is working?
  • What buying journey works for inbound leads?
  • What’s the narrative for discovery calls?

Figure out what’s working now (or make a hypothesis), write it down, and test it to see if it actually works. Keep what’s working in your playbook, and make changes to what’s not. 

And engage your team in the process of building your playbook, Kevin says – there’s no reason to tackle it all by yourself.

🤔 How do you know when you need to change your selling process?

Kevin wants his team to celebrate their losses just as much as they celebrate their wins. For a fast-growing company like Clockwise, it’s critical to constantly learn as they grow.

When the team is open about their losses, it not only helps them improve their sales processes, but also creates the right culture of not being afraid to learn from failure.

Kevin also does a lot of ride-alongs on customer calls with his team, so he can learn what’s working and what’s not through observation and feedback. “We’re always learning from our customers, and they’re guiding us,” he says.

💡 Kevin’s top sales recs

  • Book: New Sales. Simplified. and Sales Management. Simplified. by Mike Weinberg – classic, universal sales advice on winning more new sales and leading teams
  • App/software: Scratchpad – it’s finally a tool that works for the reps
  • Another sales team you admire: Figma –they’re winning a ton of accounts and have helped reshape the market

About Kevin and Clockwise:

Kevin Nothnagel is VP Sales at Clockwise, and previously built sales teams at Productboard, Facebook, and Dropbox. He joined Clockwise to build the sales team and help organizations everywhere find more Focus Time to be happy & productive at work. Clockwise automates many of the everyday chores of managing your team's calendars and is used by over 10,000 organizations such as Netflix, Atlassian, and Uber.