BTM Q & A : Head of Sales at Crew App – Brendan Darby

Welcome to the first BTM Question and Answer session of 2017!  Our goal is to find sales leaders that are on the cutting edge of management , sales technology, sales process, and interview them in order to share their learnings with the community.

For today’s Q & A, we’re speaking with Brendan Darby, Head of Sales at Crew App, a mobile messaging app that helps shift workers communicate more efficiently.

How do you strike the balance between analysis paralysis (trying to measure too much), and flying blind (not measuring anything)?

I try to measure absolutely everything. I’d rather have the data and not need it than need it and not have it. The more you can take the burden off your reps to log data, the better.

So with that in mind, you should absolutely know the two or three KPIs that dictate success in your org. If you don’t, establishing those is paramount. Your top performers should really stand out when comparing them against the rest of the org with these KPIs. If that’s crystal clear, then the organization should buy-in to the use of those KPIs. If you’re happy with your top performers, you likely won’t have to spend a ton of time looking into metrics outside of those KPIs, but it can be helpful for struggling reps to look at other metrics.

For example, maybe you know the top performers are the reps who do the most demos. Instead of just telling a lower performer to “do more demos” and collecting your manager of the year award, sit down with them and dive into the metrics underneath those KPIs. What’s their pipeline composition? Is it too heavy in one vertical or geographic area? What is the frequency with which they’re reaching out to their opportunities? How many touches before they give up? Monitoring the obvious metrics is table stakes to a manager, but measuring everything so you can do deep dives is an effective way to turn your C players in to B players, and your B players into A Players.

What interactions / meetings should managers be having with their reps and why?

Roll up your sleeves. Managers should be with their reps all day every day. Seriously…what else are you working on that’s more important??? You’re a manager because you have the knowledge to help them grow and succeed. You are not doing yourself or your people any favors by hiding behind a laptop screen. Here are a few things you should be talking to all your people about, every day:

  • What’s on the calendar?
  • What does the pipeline look like (any glaring problems)?
  • What are they hoping to get done today?
  • What important demos do they have today?
  • You can ask a million sub-questions from this question. You’ll notice trends over time that turn into learning opportunities (the 4th time you hear “well she’s not the decision maker, but…” you should know it’s time to have a conversation with the rep or the SDR).
  • How can I help?

The coaching and pipeline conversations should be happening every day at your sales reps’ desks. They’ll soak up info like a sponge. And when you’re really doing it well, it turns into a virtuous cycle, where you approach them and they start telling you the things they know they need to be working on without even being prompted. This allows 1:1s to be much more conversational and big-picture. Which leads to the next question:

What’s the best piece of advice you’ve received from a mentor?

Have a 30-60 minute 1:1 with every direct report, every week, no matter what. It’s amazing how many people that I look up to have stressed this to me, and also how many managers I’ve encountered that can’t be bothered to do 1:1’s. Furthermore, I’ve seen lots of sales managers that treat 1:1s as an opportunity to catch up on what’s happening (which they should already know from the questions above).

When you’re rolling up your sleeves and you know what’s happening with deals/demos/pipeline, etc, you can talk about things that aren’t normally discussed when you’re sitting down at someone’s desk. Use this time to really get to know your people. Where are they from? What is their family like? What do they like to do away from work? Why do they want to do sales? What do they aspire to? What impact do they want to make on the company? What do they want to do with their career?

These conversations help add a personal side to your professional relationships. For those that work in Silicon Valley, building relationships in this manner is especially important, given that you can bet all of your reps are being hit up multiple times per day on LinkedIn. If your reps feel connected to the company and their manager, your chances of keeping them around are astronomically higher.

How do you get buy-in from the people you manage?

“Earn the right” is a mantra I try to live by. Have you earned the right to crack the whip? Not if you haven’t set a clear expectation first. People rarely get upset when there are consequences to underperforming in a situation where clear expectations were set; they get upset when their manager jumps on them for something they really didn’t know was expected of them in the first place. I can tell you first hand, it sucks! Don’t do it. As a people manager, you have a sacred duty to be consistent with your people. You get buy-in from setting clear expectations and holding people to them without fail. Be respectful.

These things all build on each other. If you’re establishing early on that you’re willing to take the time to sit with your reps, teach them, encourage them, help them grow, etc. then they’ll feel empowered in their 1:1 to be open and honest with you. The trust will continue to build from there and you’ll find that you’re rarely caught off guard by anything. Because ultimately, that’s what “buy-in” is; trust.

Most important thing to learn for new sales managers?

  • Whatever worked for you may not work for everyone you manage. There is no one “right way” of doing things.
  • Wasn’t it great when you were a top sales rep? You were showered with love and affection. You need to do that to your reps too. And get used to not getting love and affection anymore. It’s no longer about you; it’s about your people.
  • Don’t create stories about why one of your reps said or did something. Have a conversation with them about it. Go into the conversation with the most respectful interpretation in mind. You’ll be shocked at how different the dynamic of the conversation will be than if you go into the convo prepared for a battle.
  • Cut yourself some slack. Managing people is hard.


Brendan Darby is the Head of Sales and Customer Support at Crew App, where he oversees all things customer-facing. Prior to Crew, he spent nearly eight years at Yelp, starting out as one of the first 25 sales hires. In his time there, he held various titles, conceived and built multiple leadership training initiatives, closed the first large-scale (250 location) local cost-per-click deal, wrote for the Official Yelp Blog, and interviewed Steve Young at an all-hands.

He has also been a VP of Sales at Accelo, co-founder of Relentless Foundation, a non-profit aimed at mentoring high school and college football players, and a lousy NFL offensive lineman for two years.
He lives in San Francisco with his wife, daughter, and three rescue mutts.