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5 Takeaways from our Spring Meetup with Michael Chessa and Paul Turner (Recap)

Every quarter, 321 rounds up our community to learn from our friends in high places. With the last meetup featuring some of our favourite marketing minds, it only made sense for our spring edition to focus on sales, with Paul Turner of Chata.ai and Michael Chessa of Tugboat Logic co-headlining.

The topic? Managing high-performing sales teams and the session was chock full of gems! We’re sharing a few nuggets for those who couldn’t join us, but are still looking for some tips on managing their sales team.

Our Speakers

Paul Turner (PT) is the Chief Revenue Officer at Chata.ai. Paul believes in building future-proof businesses with the help of powerful, leading-edge technology. Previously the Director of Growth at Skip the Dishes, Paul now lends Chata his extensive experience creating teams and bringing disruptive products to market. He is passionate about tech and enjoys the challenges of building start-ups.

Michael Chessa (MC) is the VP Sales at Tugboat Logic. He has spent the last 15 years in the tech ecosystem focusing on the one thing he’s extremely good at – helping SaaS companies grow their businesses. At Tugboat Logic, he’s been the key leader in expanding the sales team from 0 to 100 people, and growing their client base from 0 to 750. Along with this extreme growth, he’s developed a great working culture for new and experienced talent.

“High-performance” varies

The first thing to understand when managing a high-performance sales team, is that “high-performance” varies, depending on your situation.

“From a startup perspective, I’m looking for people who are able to adapt, and people who are able to test and experiment.” says Paul Turner. “You’re not only looking for people who are able to understand business, but you are looking for people who are able to contribute to that feedback loop. At Chata, we always wanted our rev gen (revenue generation) team to be aligned with our product and tech team, so it is not abnormal for product marketing to be on our sales calls, and it is not uncommon for our sales people to be at our product team’s stand-ups.”

“From a scaleup perspective, it’s all about execution. You are therefore looking for proven folks that have the ability to perform well in an existing sales engine”

“I agree with Paul. Early on, I think the most important thing is having good feedback loops. You also need to find product-market fit and start building a sales model that fits the buyer.” adds Michael Chessa “Then, the scaleup phase is about doubling down on your model and knowing when to pivot if your model isn’t working.”

To have a high-performing team, you need high-performing people

When hiring a salesperson, consider the stage of your company, and hire accordingly. There are a few attributes Michael looks for when adding to his team: “It sounds obvious, but you need to hire smart people. In a startup, there’s a lot of stuff that’s undefined so they need to have the right problem-solving ability and perspective. That, plus a good work ethic and good character, makes for something special.”

Paul prioritizes looking for grit when hiring. Whether it’s a salesperson or another member of your startup team. But what does grit look like?

“It’s a lot like love, I don’t know how to explain but I know it when I see it! I think there’s something about the trials and tribulations of sports, having to grind in the corner everyday and the experience of playing on teams – both good and bad – that leads to grit. If you look at the 90s Bulls, a guy like Michael Jordan just had a level of intensity that you knew was going to carry his team to the next level.”

Hire! But tread with caution….

Early on, there can be a lot of pressure to hire for sales, whether it be an experienced salesperson or a someone who’s keen on getting experience. In both cases, Michael and Paul encourage founders to exercise caution.

“The earlier on you are, the more you want to double down on their (the new hire) ability to execute. If you take someone who doesn’t know what they’re doing, as a startup, you may not have the infrastructure or the sales enablement available to help them be successful.” explains Michael.

“Unless they can sit with someone who knows what they’re doing and can help them struggle through it for the first 3 months, you’re writing a death sentence”.

Paul adds “I think it all depends on context. On one hand, I am willing to take a flyer on someone who is young and inexperienced, but right now at Chata, I’m looking for someone with experience, so it’s not always black and white. On the other hand, I am a huge believer in “Founders need to sell”. You need to fall in love with selling because the only person who is going to figure it out is you.”

“I think it’s also important to understand the lifetime value of your customers (LTV). If my LTV is small, I am probably looking at digital marketing, if it’s somewhere in the middle, I’m looking at SDRs. If it’s something like Chata where we keep customers forever, it’s a way different model.”

Make sure your team is well-equipped

Paul and Michael discussed the need for transparency between sales and product. It’s a unique challenge given the test-and-experiment culture of startups. Michael recommends using call transcription tools such as Gong, Avoma or Chorus.

“It really lets you get a pulse for how people are reacting to your product. They help you take a snippet from a call, that you as a salesperson can’t communicate as clearly as just having your product team listen to the customer say ‘hey I need you to do this’. If it’s a salesperson delivering that message, it may not land as effectively.”

Compensate accordingly

Creating compensation models is difficult and demands a delicate touch. In early stages, it can be tough to figure out how to create a success-based compensation structure when you aren’t selling at a high-volume.

“Again, I think it depends on the stage of your company” states Michael. “If it’s an SDR or a BDR, you can compensate them on meetings or pipeline generated. If it’s a full-on rep, I would probably stick to the 50/50 model (a base salary + commission). The key is to make their targets realistic.”

Paul was quick to add “I get really frustrated when corporate people get into startup environments and try to impose what works in a corporate environment into a startup or scaleup, because it doesn’t work. Some of the models that are coming out are so complicated that salespeople can’t even calculate it. To be blunt, if I can’t calculate my compensation on a napkin, it’s too complicated.”

“For that reason, I am willing to pay more salary on the front end, than I would be if I was in a corporate environment because they (the salespeople) are taking on more risk.”

What’s Next at 321

Your next chance to connect with 321 will be at our Growth Snack, all about copywriting on Wednesday, May 26th. Watch us optimize sales emails in real time! If you’d like your email optimized, send one in to hi@321growthacademy.com.

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