My job resume reads long when considering the several startups I co-founded. But as a full-time W2 employee, there’s been four since college. There was IBM Global Business Services, Chainnovations (acquired by Chainalytics), SalesWise (including Burner Rocket, acquired by VLG Marketing), and now, AUTIT. In each opportunity since IBM, though, I never applied. They came from deliberate, sometimes cold, outreach from me. What set these job acquisitions apart from traditional hiring processes was that each started with consulting as a test of how we would work together.

I’ve applied seriously three times since my initial post-college job at IBM. Two of those, I withdrew my application after initial rounds. My experience ranges from large corporations (including my co-op with UPS during college) to early-stage startups. The two opportunities I withdrew from were companies between 50-100 employees. They were firmly in the growth stages. My interests lay in building early companies rather than just scaling.

When evaluating new opportunities, I’ve been fortunate in timing of companies in their stages. But also, I have enjoyed showcasing my capabilities while also evaluating the company’s fit – creating a consulting arrangement first. Here’s how this process has worked out for me:

  • Chainnovations. I worked with IBM Global Business Services as a Logistics Consultant straight out of college 2008. However, the economy was tanking, and in March 2009 while I was in between projects, I was informed I would be let go in 30 days. Turns out 36% of my group was joining me. Within 30 minutes of that call, I looked up the company my friend worked at. He mentioned months before it was a very small company, like a startup. I figured I could give this a try and learn as much as possible, so I could learn about starting a company in the future. I called the number on the website. Turns out, I was talking to the CEO and Founder. Since I had 30 days of pay till being let go from IBM, I offered him free work as a “test drive”. He agreed, and within 30 days, I had an offer to join. I had a job before I was let go from IBM; whereas, many of my fellow IBMers took several months to land on their feet.
  • SalesWise. After Body Boss, I started a consulting shop called Five Points Digital to figure out my Next Big Move. I consulted on sales process improvement projects to supply chain to app and from website build to project management. I wanted to network and find problems to help inspire my next startup. Problem was that I didn’t unearth that aha idea. At the end of 2015, I ended the consulting shop, and made the decision to join an early-stage startup to learn how to scale. Almost the exact next day at a coffee shop in Atlanta Tech Village, I saw the CEO and Founder of a startup I had met two months ago while I was consulting with another company. I told him I was looking for my next steps after I finished writing my book. We sat down and agreed on consulting work for a month to evaluate working together. During my time, I focused on helping launch marketing campaigns for the company’s new product while providing input on a sales structure. Within two weeks, I had an offer from the company to join to which I accepted.
  • AUTIT. This is fresher given I just received and accepted the offer two weeks ago. After the sale of Burner Rocket, I was transitioning out of the company the rest of the year. That meant Jan 1, I would no longer be employed. I had been evaluating options for my Next Great Move since the acquisition anyways. Problem was that I didn’t have any ideas or problems I was passion about. Nor was I excited about the macroeconomics for 2019-20. I also recently got engaged. 2019 was going to be the year that required greater stability. Thus, I was on the lookout for other full-time opportunities. Serendipitously, I read about a startup in the supply chain space having raised $2.7M seed round. After a quick review on LinkedIn suggest they were extremely early-stage. I dropped a couple messages to the CEO and COO over the next week expressing my interest to speak to them. I eventually got a reply from the CEO to sit down. Subsequently, I met with the other co-founders (COO and CTO), and we agreed on consulting for the next two months. I had started a different supply chain consulting project for the rest of the year. I was only able to offer AUTIT a handful of hours to which they were eager to try. However, the supply chain contract never fully took off, so I was able to shift my time over to AUTIT. With the supply chain work cancelling, the AUTIT team offered to bring me on full-time earlier. Within 1 month of our contract, the team extended me a formal offer.

Quick notes: It was after Body Boss and before SalesWise when I consulted with several companies. A few companies and I worked together to explore working full-time after our initial contracts. However, none of those materialized into full-time positions. Those initial consulting arrangements allowed responsible parties to realize we were not good fits. I learned about how teams worked together, trajectory of the companies, etc. Early consulting allowed me to dive in without risking longer term objectives.

Before AUTIT (and after Burner Rocket / SalesWise), I applied to Google. This would have been a good opportunity to be a part of a company that was at the cutting edge of technology. Meanwhile, they would pay well and make up for the deficits of working in startups over the years. This would have been a deliberate move to learn and build up a seed fund for a future company. However, this hiring process didn’t go too far.

What’s all this mean to folks looking to make moves? Paths can be very different than the traditional apply-interview-offer format. My path has been relatively the same the last several positions. My motivations have changed, but I have aligned goals to the process I felt would be most advantageous to the value I would bring. I don’t “interview”. I don’t “apply”. Though I keep an updated resume together, I have not used it much – certainly not for my last several positions, not even during our early talks. I know my value, and it does not fit on one page.

Figure out what works for you. Then, try to control part of the process to put you in the best position to achieve your goals.

Big news! I’ve joined another early-stage startup here in Atlanta called AUTIT.It’s been almost exactly three years since I started consulting with SalesWise which led to full-time employment in February 2016. But I officially close the SalesWise (and Burner Rocket) chapter in my life today as I officially start with AUTIT.

SalesWise has been a tremendous journey where I learn so much. It’s odd looking back trying to piece together if I learned as much as expected, more, or less? All I can say is that I learned in every aspect of the growth side of business – from marketing to sales to customer success. Though, we did not scale as much as we all hoped, I got to experience real, structured processes to drive growth. I got to create a whole new go-to-market strategy that became its own product and business (that was later sold – Burner Rocket). I spoke to hundreds of sales leaders and their team members and got to understand what made sales leaders successful. I got to understand what they assessed from their sales professionals. I got to work with executives from marketing to customer success. I sat in on Board Meetings and met highly successful entrepreneurs and venture capitalists.

Then again, I got to learn a lot about what did not help drive growth. I learned about misalignment in product positioning as well as the criticality of customer discovery for true pain. I learned the side effects of taking on moderate venture capital early on. I learned the traps of building based on financial proformas from a top-down rather than a bottom-up model. The careful scrutiny of burn rate was more apparent than ever.

And of course, I got to experience growing a completely new idea into a product and into an acquisition with Burner Rocket. I experienced the negotiations processes with some due diligence. Burner Rocket was successful not just for us, but for many of our customers, too. It’s now a checkmark in my many boxes for success.

I could go on and on about the incredible almost-three-year ride at SalesWise, especially talking about the relationships I’ve built and forged. However, it’s important to now translate those lessons learned and continue to forge those relationships to this next chapter at AUTIT.

I will explain how this opportunity came in a future post, but for today, I’m excited about the prospect of blending my diverse experiences into a single entity. AUTIT dramatically reduces inventory costs through data harmonization for the world’s most complex supply chains. Here, I can leverage my experiences in supply chain and consulting as the industry and personas while coupling my technology and startup experience into this new role at AUTIT. Here, I am employee number 7. I will start this journey as a Solutions Architect – building the bridge between product and growth teams. That’s simply the title to get the job requisition passed. However, I will also help handle marketing, product management, account / customer success, and be involved in the sales process. The title is focused, but my role is multi-faceted. Perfect.

It’s a good story on how I came to this day. I’ll save that for another day. For today, cheers for new chapters that continue to build on the story.

Since selling Burner Rocket, I’ve been working on finding the Next Great Move. This could include starting another company, joining another early-stage startup, or go somewhere where I can make good money – save and pursue my own company later with seed funds. However, now, I’ll need to consider a big next phase in my life – marriage.

My last post was supposed to go out on Wednesday per usual, but instead, was published on Saturday – three days later. Why? Because I was proposing to my then-girlfriend on Wednesday up in New Hampshire in the snow. (!!!) Yup! I’m going to have to edit my timeline soon.

In any case, I’m looking at three primary categories for what I do next:

  • Start another company. Pros: this is what I want to do. It’s what makes me the most excited. Cons: I do not have any clear interest in any one idea. Also, the SaaS market is highly saturated in marketing and sales, where I’ve spent my last two years. There is no clear wages here. (Danger given my upcoming nuptials and next-life-phase pieces like kids and new home.)
  • Join an early-stage company. Pros: continue to down the entrepreneurial path with some exit potential. Able to be a part of an early leadership crew to grow a company. Build something great from nothing/ little. If funded, can mitigate wage concerns. Cons: I would not be the entrepreneur, only entrepreneurial. How much of wage concerns can be mitigated? Will there be an ownership stake that enables some financial freedom upon a potential exit? Product-market fit may not be achieved and depending on leadership, leading the company to this point can take a long time… or never.
  • Join an organization that pays extremely well with learning upside. Pros: Can build up a cash stash to seed a future-startup. Will have less of the emotional roller coaster and be more even in stress-levels, likely. Can learn and network with vast resources and backing. Cons: Less entrepreneurial, if at all. Could be tied to golden handcuffs and never return to startups.

The point is to pursue one of these options early into 2019. Till then, I’ll continue filling my time with some consulting work to keep my mind sharp while learning and networking.

If you were taking a dive into another phase of your life, how are you evaluating your options? Why would you lean one way more than the other? What risks are you taking on?

Tip: if you want to change jobs, roles, careers, think about what you want in the grander picture (“vision”), and why your current situation is not fulfilling that vision. Don’t focus only on why you’re not “happy”.
There are a lot of folks who are curious of new jobs, new companies, etc. They usually have the same reasons for wanting to leave. At least, for many of the folks I meet with who want to join a startup from a large company. The last several folks I’ve met with work at large enterprises. Each shared almost the same reasons for wanting to leave – they didn’t feel valued, and they wanted to work in a smaller company where their work mattered.
Except, companies (big or small, established or startup) are all different. They differ in their cultures. True many big companies come with much structure – multiple layers. Then again, so, too, could small companies have layers. Small companies can be directed by very strong founders who have sole discretion of direction and product.
Meanwhile, adding members to the Board due to a funding event will change the expectations and execution for a young company. Many of these are outside of the control of an employee.
There should be more focus on the position today. There’s a lot to learn in every position even the role someone may be in for the last 5 years. Too often, folks focus on the bad while missing the good – what is learned and what can be learned in a current situation. By focusing on the bad, folks go searching for new roles with a short-term view to “alleviate” the bad of a current position. This can lead to consistent change and unsatisfied work. Go beyond short-term objectives and take a look at the long-term view of goals and objectives.
Steve Jobs famously said in a Stanford commencement speech, “You can’t connect the dots looking forward; you can only connect them looking backwards. You have to trust that the dots will somehow connect in your future.” This also highlights an important point in that each decision leads to another decision which leads to many, many more. It gives freedom to take chances knowing that the dots connect but having that vision of where you want to go helps make the next dot fit closer to the trajectory you’re hoping for.
Before making that next jump, even before you ever feel “unhappy”, evaluate what your vision is for yourself. Then, evaluate how each position/ jump/ dot fits into the vision including where you stand today.