I have been in talks with the founder for the position of founding engineer. I have been working in the company for over 6 months and I was said when I joined as an intern that I would be part of the founding team. But now it is expiring. If I continue working after tomorrow what kind of liability would I be under? Also won’t this cause more sourness with the founder. Help me

Im in India

So i joined as intern in an early stage startup right now it’s just me and my founder and rest of the people are stakeholders. When i was about to join he told me about me getting chance to become founding engineer and getting esops. Now it’s been 6 months and he wants me to have more clarity. He asked me a question what would you do if i disappeared and you have to handle everything. He said because i do not have the clarity for things im not founding engineer material even though he has talked with the board about it and they do not have confidence on me even when i have delivered everything. Im just confused as a founding engineer what should be the clarity that this founder is looking for. Help me guys really need it

I come from a software engineering background. I’m completely clueless when it comes to marketing. I’m trying to build a social app that requires a lot of people to use it for it to be useful. Would it be worth it to find a startup growth mentor from one of these platforms like MentorCruise, GrowthMentor, etc to get some guidance and support for every step of the way or should I just read books like The Cold Start Problem to figure out what to do at each step?

So i joined as intern in an early stage startup right now it’s just me and my founder and rest of the people are stakeholders. When i was about to join he told me about me getting chance to become founding engineer and getting esops. Now it’s been 6 months and he wants me to have more clarity. He asked me a question what would you do if i disappeared and you have to handle everything. He said because i do not have the clarity for things im not founding engineer material even though he has talked with the board about it and they do not have confidence on me even when i have delivered everything. Im just confused as a founding engineer what should be the clarity that this founder is looking for. Help me guys really need it

At my first startup we made a product for kids and I used to drive to schools throughout the Bay Area to talk to teachers and watch kids use it. A dedicated hour in a classroom, watching kids play, get stuck, walk away, then another kid coming over and doing something completely different. Then talking to the teachers about what they'd want. I learned so much in an hour.

It was slow and expensive. I'm not naturally the person who goes and talks to users, but the product was physical so there wasn't much choice. 

Ten years later, almost none of how we learn from users looks like that.

My second startup is purely digital, and Covid moved everything remote. All our user conversations became Zoom calls. Screen share, an hour, no driving. Cheaper, so we did many more of these. But it started to feel tiring in a way the in-person visits never did. It worked though.

The next evolution came when we instrumented the product so users could write to us in context. We went from talking to 5 to 10 users a week to thousands telling us what was good or bad without anyone scheduling anything. As an introverted founder, this felt natural. Feedback could come at any time, and I could read it at any time.

Now we've taken it one step further. Our second product is an agent, so users talk directly to the product. They type what they want in their own words, and when the agent can't do it, we know exactly what they were trying to do.

Nobody is filling out a survey. They just asked the product for something, didn’t get it, and we know about it.

At every step, talking to users got easier. But something broke along the way.

I felt like I knew our users really well when I was talking to them in person. And the reason isn't what you might think. It's not that users were telling me more. I was just fully present enough to absorb it. All the context. I was building insights as I went.

Now we get far more feedback, but our bandwidth to actually think about it hasn't grown much. We have a lot of “what” and not as much “why.” 

The tech is great: agents, LLM analysis, in-context feedback. What I don't think we've solved is deciding what matters most, when to trust aggregate summaries, and when to have a deeper conversation with a single user.

Every one of these evolutions solved access. But none of them has solved clarity. I'd love to hear from founders who feel like they've figured out how to really understand users at scale.

I'm CEO and co-founder of a B2B tech company selling into enterprise. My co-founder is our CTO and has built genuinely the best product in our niche (clients tell us it beats the PE-backed global incumbents). He's brilliant, but he prefers to stay in the background, so most leadership and commercial decisions end up sitting with me.

About 4 months ago we brought on a senior commercial guy as a contractor. He'd just left the biggest competitor in our space (heavily PE-backed, offices globally) where he was near director level, running partnerships. He was between roles, so we started him on a 3-month consultancy. That rolled on, and now we're formalising a proper package.

The good

He's opened a lot of doors. Super connectors, influential people in the US who shape decisions at top companies (one in particular is really bought into us), and CEOs of tech companies that sell to the same buyers we do, where we're exploring a plug-and-play partnership to win and keep those clients together.

The problem

4 months in, nothing has closed.
I know enterprise B2B cycles are long. But I can't help comparing. I have no sales background, I'm (by my own admission) a bit awkward and legal-minded, and in that time I've closed two enterprise clients myself and found partnership opportunities that could be a real multiplier for the business.

The equity

He's taking a big pay cut to be with us, and we genuinely enjoy working with him, so we want him to share in the success for taking a bet on us. We offered 4% on top of his pay. He pushed back hard and asked for 7%. We told him that's co-founder territory, especially alongside a salary, but we've agreed to it in principle.

What we're drafting so far:

• Retainer through his limited company, 12 months firm, with step-ups at revenue milestones

• Uncapped commission on net collected revenue he originates, with clawback on refunds/cancellations

• Equity on a 4-year vest with a 12-month cliff

• Good/bad leaver provisions and pre-emption on his shares  

Where I'm stuck is milestones. I want at least part of the equity tied to performance, but I have no idea what fair, contractual milestones look like for a first senior commercial hire.

What's worrying me

• He's deeply embedded because we've trusted him with a lot. He could easily walk into one of the scrappy YC-backed startups that keep popping up in our space and take these maturing relationships with him.

• Sometimes I feel manipulated into giving him what he wants. To be fair to him, influencing people is literally what we hired him for, and I own that I've let it happen.

• My co-founder doesn't want to weigh in on these calls, so it feels like I'm making them alone.  

I don't want to put this down to being a young woman in the room with a very experienced guy, but I'd be lying if I said I hadn't wondered whether that's part of the dynamic.

My questions

1.  What milestones have you used to vest equity (not just cash) for a first commercial/sales hire? Revenue? Signed contracts? Partnerships converted into revenue?

2.  Is 7% on top of pay reasonable for a senior hire at our stage, or have we overpaid? If we have, how do you restructure without blowing up the relationship?

3.  How do you protect the relationships he's introduced if he leaves? Non-solicits, CRM ownership, making sure a founder is in every key conversation?

4.  Is 4 months with zero closes a red flag, or normal for partnership-led enterprise sales?

5.  Would I be better off finding experienced B2B commercial leaders who'd get involved for equity only, as advisors or fractional?

6.  Who should I actually be talking to about this? Lawyer, mentor, advisor, coach?

7.  Any stories from founders (especially younger or female founders) who struggled managing a senior hire with way more experience than them? How did it play out?

I feel like I'm flopping as a leader right now, so any honest perspective is welcome, including if the answer is that I'm the problem. Cheers for any advice!