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.
Chuck has been in sales and sales leadership roles for nearly 20 years, and pivoted his career to launch Blueprint Expansion in 2020 with the goal of helping companies recruit and hire exceptional GTM talent. He’s passionate about the problems Blueprint Expansion solves, especially for early stage startups, and chatted with Ross about how sales teams can up-level their hiring game.
Listen to the episode here, and get the key takeaways from our conversation below.
🧠 What’s your philosophy around recruiting and hiring in sales?
Once they establish product-market fit and start to hire sellers, most companies recognize that they need a defined sales playbook to optimize growth and the buying experience. The problem is that many orgs don’t give the same level of attention to their recruiting and hiring process.
“You need a documented hiring process just like you need a sales process,” Chuck says. “A lot of early stage companies make hiring decisions based on their gut or their personal network and relationships, and that’s not the way to build a strong, values-driven org.”
🙅 What are common recruiting pitfalls, and your advice for avoiding them?
Not being aligned internally. When building your hiring process, make sure it’s documented and agreed to by everyone from your hiring manager to the recruiting team (internal or external) to executive leadership.
Hiring for experience and pedigree instead of skills and behaviors. Years of experience, the school someone went to, etc. are not as important as ensuring a candidate’s skills fit the role you’re hiring for – and that their overall behaviors and traits fit your culture and environment (i.e. adaptability in an always-changing startup).
Not defining your SLAs or being respectful of candidates’ time. Be sure to agree on turnaround times for responding to candidates, booking the next interview, etc. Err on the side of rigorous honesty with your candidate: let them know what you like, what you’re discussing internally, and when you’ll get back to them. Job searching is stressful – don’t add to it!
🤔 Say you’re a CEO or VP of Sales, and you’re looking to hire your first 3-5 AEs. What do you look for and how do you test for those skills?
Chuck recommends evaluating three key areas:
- Do they understand the problems you’re solving in the market today (who you’re selling to, why does it matter, etc.) and can they speak about it in their own words?
- Fit for the role – will they be able to tackle your specific needs and drive the outcomes you’re looking for?
- Maturity, leadership skills, and alignment with your culture – the “softer” skills that are crucial to building a cohesive, strong, values-driven team.
As far as how to test a candidate’s skills, assignments can be valuable for seeing skills in action (for example, a mock call or sample email for an SDR role, or a 30/60/90 plan for a leadership role). But don’t ask them to do a bunch of “homework” – again, be respectful of your candidates’ time and effort that goes into the job search.
If done well, and if you collaborate and give actionable feedback on these assignments, it can be a great way to build enthusiasm for the role on both sides.
⚡ Lightning Round: Chuck’s Fast Sales Insights
- The most common misconception about sales recruiting? That it’s all about “sourcing quality candidates” – the foundation has to be in place first.
- Favorite sales app/software? Calendly.
- Another sales team you admire? Invoca.
- A helpful sales book or resource? Mike Weinberg’s Sales Management. Simplified.
- The hardest part of scaling sales at a startup? Prioritization – figuring out where to put your focus and aligning with your executive team on it.
Chuck Brotman is the co-founder of Blueprint Expansion, a GTM-roles recruiting agency. Previously, he ran sales at PeopleGrove and Motive. Prior to this, Chuck worked over 13 years at ON24, where he held various sales and sales management roles. He lives in the Bay Area with his wife and younger daughter (a senior in high school).