Startup Sales Priorities: Deals, Playbooks, & Coaching w/ Clay Bentley

Seller's Journey Episode 7
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 Clay Bentley, VP of Sales at Metadata

Before joining Metadata two and a half years ago, Clay led sales at G2 Crowd for four years, and previously worked as an AE at several SF-area companies and startups. He told Ross: “Startups are my thing – they get me out of bed in the morning.”

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

🙅 What do most people get wrong when it comes to sales at startups?

Three key mistakes Clay often sees in startup sales:

  1. A lack of focus on coaching – all the focus is on hitting targets.
  2. Too much emphasis on new logo acquisition, and not enough emphasis on retention.
  3. Staying strictly within your perceived ICP, instead of being comfortable with stretching outside it and finding prospects who aren’t “lookalikes” of your existing customers.

🏅 What’s the most impactful thing you can do when coaching reps?

It’s not scalable, but one of the best things you can do as a sales leader is hold regular 1:1 time with your reps, Clay says.

AEs want to improve; most of them don’t want to be an AE for the rest of their lives. In your 1:1 time, you can learn what your reps’ goals are, help them sharpen their skills, and guide them toward leadership or whatever their next step is.

You should also give your team a platform for evangelizing themselves and their contributions. Everyone has a different “zone of genius,” Clay says – let your team use their individual strengths and have a say in your sales playbook or processes, and give them recognition for their contributions.

💡Lightning Round: Clay’s quick sales insights

  • Favorite sales app or software? Gong.
  • Another sales team you admire? Also Gong!
  • Helpful book or resource? Blitzscaling by Reid Hoffman and Chris Yeh – it was terrifying and exciting and cautionary.
  • The hardest part of scaling sales at a startup? Balancing executing deals and working on your playbook. We wake up in the morning looking at numbers and chasing numbers, and we often forget to document what works and what doesn't. 

About Clay & Metadata

Clay is the VP of Sales at Metadata, and was formerly the VP of Sales at G2. His journey has taken him from SF → Chicago → Nashville, where he currently lives. Metadata automates paid campaign execution and strategy, eliminating manual and repetitive work for B2B Marketers.

Metadata is hiring! Check out their open roles here.