Like me, Lauren McCullough did not begin her career in startups, but she found her way here after getting bored by the bureaucracy and red tape of larger organizations, and asking herself (in her words) “like, why am I mad all the time?!”
This impatience for inertia is also “probably why [she’s] never done enterprise sales”. Instead, she’s been focused on the SMB (Small and Medium Business) segment.
Recently, Lauren founded Tromml, a B2B SaaS platform that helps automotive sellers improve their eCommerce performance.
Prior to Tromml, for a number of years Lauren was a fractional sales leader at a number of startups. She found herself coming in to help early stage founders solve a recurring problem — that the first sales leader they hired just didn’t work out well.
At this point, Lauren rode in on her magnificent horse, and gallantly saved the day. (That is, she helped get growth going, wrote the sales playbook, hired the first Account Executive, and rode triumphantly off into the sunset.)
I was curious why so many founders experience this same problem in hiring their first sales person. I would summarize Lauren’s response as follows:
The founder is always going to be the best at selling the product — at least in the early years. They have the passion, the comprehensive understanding of the product and the industry, and the credibility and clout with customers. So the first “hired” sales person has to be really good (because they have to step into the selling shoes that the founder has been wearing up until that point).
And oftentimes, founders assume that means they need to hire a “seasoned” sales executive — for example, someone with 10 years of experience at Google or Salesforce. An “expert”. But the problem is that at the early stage of a startup, that sales hire needs to roll up their sleeves and grind. They need to be on calls all day long. They need to be the SDR (Sales Development Representative), as well as the AE. And an experienced executive thinks that is “beneath them”. They expect to have a team to do that grunt work. But the startup doesn’t have the budget to hire a team yet. And even if they did, the sales “leader” doesn’t really know how to train the team, because (s)he has never done the actual selling work themselves (at least, at this company — and every company is very different).
Furthermore, hiring more senior people is often constraining from a talent perspective. People who are further along in their careers usually have a much higher compensation expectation. And they might also be more risk-averse (maybe they have a family to feed, etc.). Put another way, it’s very unlikely that an early stage startup can hire the ”top 0.1%” of experienced, 35-year-old sales executives. But it’s much more likely that they can hire the top 0.1% of inexperienced but enthusiastic and energetic 21-year-olds.
In terms of Lauren’s thoughts on “what makes someone awesome at sales”:
(1) Resiliency and Grit. “Sales is really hard, because you get more No’s than Yes’s. And people lie to you because they don’t want to hurt your feelings by saying No” It’s striking to me how basically everyone I have interviewed for Closing Time so far has mentioned this principle.
(2) Consultative Sales and Active Listening. Lauren extolled the importance of a “deep curiosity”, which “is especially important in early stage startups”. One practice that Lauren likes to do with her clients is to walk them through an example of how they are currently experiencing a problem. And then replay that example, but articulate how the problem would be solved if the client was using Tromml.
(3) Work Smarter, not Harder. Lauren dived deep into this principle, and we touched on many facets of it:
Instead of just stuffing more leads in the top of the funnel (a “numbers game”), Lauren advocated for trying hard to understand the friction in your sales process, and seeking to remove it.
Seeking to genuinely add value for clients, which leads to compounding inbound leads from referrals over time.
Highly qualifying leads, to maximize your efficiency. Lauren mentioned that sometimes she even hands leads to her competitors, because she knows they will be a better fit for a client.
And thinking carefully about timing, and when a customer might be looking for help. Lauren gave an example of how someone might be experiencing a problem, and the intensity of that problem fluctuates day-to-day, or week-to-week on a scale of 1 to 10. If you can identify when it’s spiking to a 10, there’s going to be a lot more interest in purchasing. At Wefunder, I see this very clearly. Founders might be looking to raise capital every couple of years — so it’s important to highlight a community round as an option for them to consider to coincide with that fundraising lifecycle.
And some rapid-fire questions…
What do you look for when you're hiring salespeople?
“Ethical people”. “Judge character before you judge skills”. “If you have a person who’s toxic on your sales team, that will not only create a bad culture among your team, but they can also create a bad reputation among your customers, and create a lot of tension between your sales and development teams”.
What's a controversial opinion you have about sales?
Lauren mentioned a couple here — firstly, that the best sales people are not actually motivated by money. Not necessarily that a commission-based compensation structure is a bad idea. But certainly that the best people are motivated by other things as well (mission, winning, team, learning, etc.).
Secondly, “I hate most sales books. Most of them are outdated and unhelpful”. I love it!
Who's the best salesperson you know — and why?
Although she eschews most sales books and “influencers”, one author that Lauren does really respect is Chris Foss — a former FBI negotiator, who now writes and teaches about negotiation. But according to Lauren, while Chris’ content is overtly about negotiating, it’s actually really teaching you about empathy and how to problem solve. Here’s Chris’ Masterclass, if you want to dive deep.
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