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

Nerd Journey: Career Advice for the Technology Professional

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 during the interview process because he really wanted the job. Deeper questions about go-to-market to check for alignment might have been helpful.
  • “Looking back on it I’m going to blame myself more than I’m going to blame them…or anything like that. I’m the one who made the deicision to leave the big company and go to the startup…. To be fair, I don’t think my role ended up the way that my manager expected it to either. And that’s just the turn on a dime of a startup.” – Brad Pinkston
• With Brad’s knowledge of and experience at his previous employer, did taking this to a new employer play out the way he expected or differently?
  • This goes back to the difference between crafting a strategy and executing one made by someone else. In the strategy Brad wanted to build, his relationships from the previous company were going to be extremely valuable because sales teams from each company would be in active collaboration.
  • Brad’s role at the startup ended up being more focused on business development in the background – a mix of engineering, product development, and even product management. While Brad felt he was effective in doing the job, he wasn’t as passionate about it as he would have been if the role had been more of what he was expecting.
  • The relationships Brad was bringing to the startup were not valuable in the end because…
    • It was not his strategy.
    • The relationships he had did not bring value to the strategy he was given by others to execute.

20:11 – Technical Alliance Relationships

• John mentions this sounds like it could have been an ISV (Independent Software Vendor relationship), OEM, or even an alliance partnership between the startup and the big company (Brad’s former employer). How did Brad build up his relationships with these teams at his former employer?
  • The definitions of things like ISV, OEM, and alliances can differ slightly.
  • Some ISVs have a technology that is marketed and sold together hand in hand by different companies. There are also ISVs where we may not realize there is an ISV relationship (i.e. something you can buy through Amazon Marketplace that is software developed by a different software vendor).
  • Brad learned that the nature of ISV relationship and which company is involved in selling a product can vary.
  • Brad was expecting an ISV relationship between the startup and his former employer that made for a better together kind of solution. The startup was selling a version of their own product that was part of a different company’s product.
    • One possible future state was having a solution (part of an ISV relationship) that could be purchased based on a customer’s relationship with either company. This unraveled quickly.
    • Brad thought it would be an ISV relationships where both company’s sales teams would be engaging with customers together / going to market together (making his relationships very valuable).
    • The ISV relationship which ended up happening was merely Brad’s company delivering technology for another company to use as part of their own solution. This did not require engagement of sales teams at the startup.
    • John gives an example of an ISV relationship he encountered while working at Google Cloud.
    • “It gets real complicated and sticky in alliances when you’re talking about OEM or ISV or…how all that happens. I respect the people that have been in alliances their entire career because it can be a spaghetti of things you’re having to deal with….” – Brad Pinkston, on the nature of technology alliances
• This presents another job and category of job that most people don’t understand or know is an area for an entire career.
  • We’re talking about managing relationships between companies that sell complimentary products, co-sell their solutions, or have one company use another company’s technology in their products.
  • John did not know this type of role existed before he started working for a big company.
  • How products are sold, where you can buy them, how products will be marketed, what teams will be involved, etc. are far more complex than we might realize (and not a topic we plan to dig deeper on today).

26:30 – Returning to Individual Contributor

• What made Brad want to go back to being an individual contributor after being a people manager?
  • Brad still misses leading a team and helping people progress their careers, and he felt taking the role was only putting this on pause.
  • Brad thought things would be very successful at the startup, and he would eventually build a team of his own there.
  • We can be leaders without needing to be people managers, and Brad highlights the chance he was given to influence people within the startup even though he did not have direct reports.
  • “I’m going to get to build something. I’ll build relationships, sales strategy, and at some point in time I’ll build a team. So it was just a pause on managing people. That’s what I thought was going to happen….” – Brad Pinkston, on the decision to become an individual contributor
  • When Brad interviewed with the startup, was Brad’s decision to pursue an individual contributor role after previously being a people leader something that came up?
    • Brad says he doesn’t feel it came up this tiem because everyone was focused on the future of what things were going to be.
    • Brad has a lot of respect for the manager he had at the startup. Brad would be someone on the bench of talent who could take a people manager role if something changed.
    • After things started to be less successful than people had expected, Brad had conversations with people to discuss what leading a team of SEs might look like at the startup. It really did not go anywhere. Brad says he might have pursued management at the startup if he had decided to stay.
• Is it hard to get used to being an individual contributor again after having been a people manager?
  • Brad says the transition from manager to individual contributor at a new company was pretty easy.
  • Part of Brad’s role at the startup was to educate account SEs at the company on what the solution being brought to market was.
  • Brad was able to leverage some of the skills he had learned from managing people in the past as an individual contributor at the startup like the ability to make connections inside the organization.
  • At first it was strange to not have 1-1s or career progression conversations. Brad missed the ability to help someone along in their career in the way managers who care can do that.
  • Brad does not miss the “adult babysitting” side of being a manager.
    • Brad built the team he was leading before joining the startup as an individual contributor, so there wasn’t much of this.

31:37 – Managers and Interview Expertise

• John had an interesting thought. After sitting through performance reviews and interviewing incoming job candidates as a hiring manager, he should be a lot better at interviewing for jobs. John would know what the interview questions actually mean. This also allows him to make performance reviews easier for leaders.
• Brad feels like his experiences interviewing people and going through performance reviews have helped him be very direct and drive conversations with his managers over time.
  • “Whether you’re selling to a customer or you’re selling to your manager that you should get a raise or a promotion, you’re always selling.” – Brad Pinkston
• Brad also felt his experience interviewing people would help him interview for other jobs. It did in some cases, but Brad says interviewing for a second-line manager humbled him significantly.
  • “But interviewing for a second-line manager humbled me…significantly. It’s a great example of what got you here won’t get you there…. The thought process and the things that I was asked and how well prepared I was…was not in line with I think what the expectations were.” – Brad Pinkston
  • When Brad interviewed for a second-line manager role, he did not get the promotion. But one of his peers did. There are some universal things Brad learned in this process.
    • Sometimes a first line manager can get a feel for what the greater organization needs, but they might not get a true picture of it at their level.
    • “You kind of have to figure out what your strategy would be and deliver it very confidently. And you might be completely wrong….because you just don’t know what the organization is going through.” – Brad Pinkston, on interviewing for a second-line manager role
    • Brad’s strategy as a second-line manager was focused on sales strategy, expectations of the team and how he would run it, etc.
    • The person who got the job was more focused on how to bring the team together, personal development, etc. It was really important to bring the people together as the organization grew and changed. This person knew bringing people together was the first priority. Brad had this item as a lesser priority.
    • At a second-line manager level you have to present a strategy and share how the front-line managers under you will help carry it out. At a front-line manager level, the tactical things are also very important.
    • “You kind of have to set the strategy at a second-line and hope that your leaders under you are adopting and bought in and part of it as much as you want them to be…that kind of thing.” – Brad Pinkston
  • About a year into his role as a front-line manager, John’s manager left. People at that time encouraged him to apply for the open spot.
    • At first, John thought it was kind of crazy to consider interviewing for the next level of management. But, looking back, he feels like the experience interviewing (even if you don’t get it) might be a nice stepping stone to getting a second-line manager role eventually.
    • Part of this might be understanding the relationships you need to have at a second-line manager level, going in with a plan, and having it picked apart. Someone could go interview for the second-line manager role and come to understand they didn’t really know what the job is.
    • “If I don’t know what that job is, then maybe I shouldn’t be applying for it.” – John White, talking about the role of a second-line people manager
    • Brad says the second-line manager job he referenced and the needs of it would be different than it would have been for the same role on the other side of the US, for example.
    • “That’s why it’s always good to be interviewing. It’s a skill you that need to continue to hone just like your technical chops. I learned so much during that process that will help me the next time that I interview for a second-line manager role….if that’s in my future.” – Brad Pinkston

38:40 – Running Away from Something

• Brad eventually left that startup and went to another startup. He felt burned out, and the reorganization did not work out the way he wanted.
• “And so I went to another startup, which…it was the thing that nobody should ever do. I was running away from something as opposed to running to something.” – Brad Pinkston, on leaving one startup and moving to another
• Brad says this was a much smaller startup, and he was eventually laid off. It was definitely a low moment.

Mentioned in the Outro

• We can’t talk about being a builder without talking about Episode 148 – The Magic of Building with Chris Wahl (1/2). It’s a great episode to go back and reference.
• People who like to build things like creative control over what they are building.
  • In Episode 244 – An Array of Decision Points with Tim Crawford (2/2) we heard about the decision between people leadership and individual contributor being a choice between building people and buidling technology.
  • At the startup Brad was trying to build something related to technology and not necessarily developing people as a manager would, so it aligns with what Tim Crawford shared with us.
• Technical alliances could have a career option for you. We’ve not highlighted these roles on the show before now. Every technology company has these types of roles that work on things like integration, OEM relationships, or ISV relationships.
• If you’re thinking of joining a startup, it makes sense to ask each person in the interview process how clearly defined roles and responsibilities are at the company and how clear each person is on their roles and responsibilities.

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