Go-to-Market: Startups and Technical Alliances with Brad Pinkston (1/2)

What exactly is a technical alliance? Technology companies create alliance relationships to support product integration and to increase revenue by creating multiple avenues for selling a product. But as Brad Pinkston knows, alliance relationships between different companies can become quite complex.

This week in episode 305 we’re rejoined by Brad Pinkston to hear his story of pursuing a role at a startup while at the same time making the move from people manager to individual contributor. We’ll define go-to-market strategy and how that related to Brad’s role at the startup, discuss what happens when a new job turns out to be different than what we expected, highlight some thoughts on evaluating startups from a different lens before joining, and listen to Brad reflect on his experience interviewing for a second-line manager.

Original Recording Date: 11-21-2024

Topics – Brad Pinkston Returns, The Allure of Startup Life, Go-to-Market and an Expectations Mismatch, Technical Alliance Relationships, Returning to Individual Contributor, Managers and Interview Expertise, Running Away from Something

2:!7 – Brad Pinkston Returns

• We last spoke with Brad Pinkston back in 2020. What has he been up to since? You can find our previous discussions with Brad here:

  • Episode 83 – The Path to People Management and Early Lessons Learned
  • Episode 84 – Management Interviews and Transitions with Brad Pinkston

• Brad decided to leave a big company and try out life working for a startup while at the same time making a move from people manager to individual contributor. Eventually Brad transitioned out of startup life and has returned to a big company in a technical presales role.

3:21 – The Allure of Startup Life

• What attracted Brad to startup life, and what makes it alluring when you work for a big company?
  • One reason to join a startup is the potential for a very large future payday from stocks.
  • “Fundamentally what I really like to do is I like to build things from the ground up.” – Brad Pinkston
    • Before moving to the startup, Brad was in a first line manager role at a big company. At the time, Brad did not feel he had the amount of control he would have liked over what he was building.
  • Moving to the startup was a chance to go and build an organization. Brad’s role was going to be leading the relationship between his past company (the big company) and the new company (the startup). The startup planned to have an OEM relationship with the company he was leaving.
  • More specifically, Brad was going to…
    • Help the two companies work together
    • Develop sales strategies
    • Teach salespeople at the startup how to work with sellers at the former company
    • Teach sellers at his former company about the startup’s new technology – something much more security and networking focused and out of the area of expertise of his former company
• Nick sees Brad’s move as an adjacency with some good relatable experience. *Brad was a people manager who had built and led teams. He would be building an organizational structure in terms of processes and ways of working together. And he also knew the technology from his former employer. With solutions from the former company being integrated into the startup’s technology, Brad wasn’t starting from nothing. His base of knowledge was very relevant to what he would be doing.
  • “Any time I transition between roles…I’m always up for a new challenge, and that’s why any of us take on new roles. But, I try to make sure that there’s a cornerstone of my skillset that’s going to be translatable…. My thought process was that I understood the tech…and I understood the relationships and go-to-market and the way that this was going to work. And I will say that I was 1 for 2 on the 2 things that I thought were going to be the cornerstones there. I did understand the tech really well, but the way that the relationships were going to work and what my role was really going to be, I was completely wrong about.” – Brad Pinkston, on moving to the startup

7:08 – Go-to-Market and an Expectations Mismatch

• How would Brad define go-to-market?
  • Brad learned from his experience that go-to-market means different things across different companies. Another thing to consider in all of this is the OEM relationship mentioned previously and the natural requirement for two companies to collaborate (the big company / Brad’s former employer and the startup).
  • To Brad, go-to-market at the startup was going to be something like the following. And he admits to being very wrong about what it actually was.
    • Interfacing with sales teams
    • Creating sales strategy
    • Be at the forefront of selling and meeting with at least some customers
    • Developing the target persona to sell to / spend time with
    • Developing the value proposition of the solution
  • “What I actually ended up getting is kind of what I felt I was in before.” – Brad Pinkston, on the experience at a startup not being what he expected
  • Brad did not get to develop the go-to-market strategy at the startup as he had hoped. He was told to execute a strategy someone else had already developed.
  • Brad also thought the startup would have a more collaborative culture than it did. Despite conversations about what he thought the go-to-market should be with many people, his ideas for further developing the strategy were not really considered.
    • Brad spent a lot of time trying to clear up misunderstandings between the two companies (the startup and the big company), but it ultimately was not fruitful.
  • Overall, Brad was not able to make the impact he originally desired.
    • “When you’re kind of a builder / engineer mindset like I think we all are…you want to see that impact. Whether it’s a check or big deal or happy customers or you just feel…a sense of success you’ve gotta have some kind of payoff of impact…and I didn’t feel like I had any at the end of the day.” – Brad Pinkston, on the importance of making an impact
• Nick highlights Brad also lost the ability to do creative solutioning in his work.
• Brad shares some lessons learned on startup life.
  • Thinking of startups brings to mind characteristics like collaborative culture, flat organizational structure, being a jack of all trades / the ability to do a variety of different types of work. You normally hear about a lot of hard work but also a willingness of people to pitch in and help wherever needed.
  • “Not all startups are created equal.” – Brad Pinkston
  • One thing Brad didn’t hear about going into this was the different inflection points of a startup’s life.
    • Brad joined the startup in question from a timing perspective during an inflection point that was somewhat detrimental.
    • When an organization is very small, employees are willing to help out in all kinds of areas even if outside their normal purview to help the company or team achieve its goal. People often work across many areas with an “all hands on deck” mentality.
    • As an organization grows, a good leader will recognize the inefficiencies and transition to having clearly defined job roles and responsibilities for each employee. We might even call this a growing pain of an organization. Brad tells us the startup was in the midst of this transition when he joined, and employees were encouraged to work within their own roles and responsibilities. This stage of the startup was not something Brad expected to encounter and inhibited his ability to impact and execute on a strategy the way he was hoping to.
    • “I thought that was the startup I was joining. But it had hit this inflection point with size and revenue and all that they needed much more definition of roles, and they were still building that when I came on board.” – Brad Pinkston
  • Just like go-to-market can mean many things to many different people, startups can go from 3 people working in a garage or home office to multi-million dollar organizations with hundreds of people on staff. John mentions we’re talking about understanding a startup’s stage of growth before joining and making sure our expectations of impact in a role match what the company expects based on the culture they are building.
    • Brad does not recommend the mess around and find out mentality to learn what he ultimately ended up learning. But he respects the fact that the startup needed clearly defined roles for its employees.
    • Brad thinks perhaps he could have had different expectations going into the role or selected another startup as his employer.
    • Large company can also mean different things to different people.
• John thinks it would have been hard to discover the startup was in this phase of growth during the interview process. Asking someone a very pointed question about this in an interview gives you one person’s honest perspective at a point in time, and it may not reflect the reality you experience when you start working in a particular role because something changed.
  • Brad thinks maybe he didn’t ask as many questions as he should have dur