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Lessons from My First Year Working at Startup

One year ago, I announced I jumped full-time with a startup called SalesWise. It had been several years since I had worked for a company (April 2012, I left Chainalytics and the corporate/ consulting world). They say one year in consulting is like working seven years in “corporate” job. I’d say that’s more fitting to say from my one year at SalesWise, and hungry for more.
SalesWise is still an early-stage company. When I joined, I was the first business hire. It enabled me to get in on the ground, and start building out… well, everything – sales, marketing, customer success, and more.
A few lessons learned:
  • It’s been a lot harder. When I joined, I was thinking, “wow, the product is great! The two founders are experienced. The CEO has even started four with all four successful exits. This will be a rocket ship!” Not so much. Modern B2B sales is harder than most people think. Every new startup is a new company with, likely, a new idea. There are tools to make things easier, better equipped, but it’s still very, very hard to build a company.
  • I’m doing what I feared I would – keep wanting to do more. I joined the company because I felt I was starting to distrust others. I joined to help me trust working with others. But no matter what, I catch myself wanting to do more, so I don’t have to rely on others. I think to myself how can I learn to program some, just so I can help speed things up. It’s crazy. I’m already manhandling the other sides of the business. I want us to be successful, and I have this insatiable hunger to do more – to test, to deliver, to sell. I need to specialize on my side of the wall, and let others specialize where I don’t.
  • There are so many tools to help a company… and confuse. The number of SaaS tools available for companies is daunting. There are so many analytics programs, customer success tools, support apps, marketing platforms, etc. It’s a dizzying array of programs to help a company know everything that’s happening, and to keep the company buzzing. However, it can be too much. I have four screens around me – most split-screened so I can monitor everything. Is it too much? Maybe. The key is using each tool effectively for what it’s supposed to do.
  • A passionate, highly intelligent team members is more amazing. I didn’t meet everyone at the company before I joined. However, it’s been fascinating the personalities at the company. Each person is highly, highly intelligent – perhaps the smartest folks I’ve had the pleasure of working with. Most are very passionate about the direction of the company, and they truly own their areas of expertise. We have plenty of passionate debates during team lunches. They’re all healthy, and they give perspective to create the best approach.
  • Following a highly successful leader who is also very transparent and honest is… amazing.I can’t tell you how often I’ve been amazed at how my CEO has been open about our company’s direction and funding. He’s listened to everyone’s input, and though he may disagree at points, he hears us all out. He’s taken time to share his intentions while looking out for our own ownership stakes in the company, and he’s making decisions in the best interest of us, our customers, and our investors. There hasn’t been as much of explicit 1-on-1 mentoring with me, per se, but I’ve been absorbing everything just in everyday interactions. It’s been fascinating, refreshing, and hugely motivating.

When I started, we were launching a product for sales (reps and leaders). We had no customers. We pivoted a couple times last year before landing on our current direction. We’re now selling specifically for sales leadership. We have a dozen customers who are passionate about what we’re doing, and we’re seeing engagement numbers climb steadily. Our close rates are incredibly high at about 4 of 5 trials converting. We just raised $1.3M to build a repeatable customer acquisition process before cranking up the machine. We’ve hired several sales professionals, and are now in the market looking for a marketer. We’re building out the Business Relationship Intelligence category. It’s going to be an exciting next year.
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TAG Sales Leadership Panel Take-Aways: High Velocity Sales Organizations

I attended a Technology Association of Georgia (TAG) Sales Leadership event a couple weeks ago on High Velocity Sales Organizations.

(I’m a little late to posting this. Having scaled down to one post a week as I round up 100 Strangers, 100 Days (today’s day 89!), my posts are being stretched out.)

The event headlined:
My take-aways from the event:
  • It’s hard to get the attention in sales, right? Every second counts – literally. The first 10 seconds are to earn a minute. Prospects are looking to be interrupted – pattern interrupt. Kyle mentioned how he was interrupted by a great cold call. Kyle told the caller to “email him later” because he was busy. The sales rep responded with, “are you sure you want to do that?” Kyle was taken back. “What did you say?” The sales rep responded slowly this time, “Are you… sure… you want… to do that?” At that point, Kyle was unsure. Kyle gave him the time. Or another cold call, “Hi, this is SO-SO. How do you handle cold calls?” It broke the ice.
  • Modern sales orgs are challenged to find the balance between “analytical scalable, measure” and “human, empathetic, customer-centric”.
  • Brian has a great track record of growing sales teams from the ground up. At Rubicon, Brian has grown from 1 to 85 sales reps in 10 months. Brian shares the keys to growth are: evangelizing the company message and vision; enable sales professionals to be pioneers; and separating the volatility of sales processes to an innovation team. What works then, gets implemented with the sales team.
  • Wanda shared how she grew from old-school orgs to very dynamic sales organizations. She recognizes the aspects of sales she can affect and what she cannot. She cites the importance of dumping baggage (possibly rigid sales professionals who do not align to the culture). Look for people who are agile, and enable them with the right tools – right tools in the right hands of the right people.
  • Brian also highlighted how the culture of sales people have a consistent theme from previous lives (applicable beyond sales, too). He looks for hustle. Can this person hustle? Is this person intrinsically self-motivated? Can candidate be beat down over and over again, and keep going? He looks for resiliency. To assess this, he tries to get the other person to open up about vulnerable moments.
  • Wanda stresses the importance for excellent communicators. If the email is trash, it says a lot. She’s looking for someone who is aggressive for the job in email. Customers will see the same type of emails. She wants her team to have lots of empathy. Be researchers and technologists – seamlessly pivoting between sales and marketing.
  • Tyce describes three types of people – 1. Person you can tell what to do, and it’ll happen. 2. Just won’t get done. 3. With no instructions, it’ll get done no matter what. Understand the different types and how the generations of people may affect them.
  • Two suggested sales books – 1. Message to Garcia by Elbert Hubbard. 2. How to Win Friends & Influence People by Dale Carnegie.
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