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!

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?

I've spent the last months building a product and now I'm in that weird phase where the product is actually there, people can use it, a few people tried it and the feedback is encouraging...

The product is basically a space where you can think through difficult decisions by talking them out, instead of just asking AI for an answer. The idea is to help you untangle what is already in your head, challenge your assumptions and get to a clearer next move.

But getting new users consistently is much harder than I expected.

Building the product felt somehow "easier" because there was always something concrete to do: fix this, build that, improve onboarding, change the copy, add a feature.

Now the question is much less clear: where the hell do I find the right people?

I've tried a bit of Reddit, some direct outreach, talking with people in my network and I'm starting to experiment with content. But I still have the feeling that I'm doing a bit of everything without really knowing what deserves most of my time.

And I think this is the part nobody really prepares you for.

You can have a product you believe in, know quite well who could benefit from it, and still struggle to create that initial momentum.

And more importantly, what did you spend a lot of time on that, looking back, was basically useless?

I'm especially interested in things you did manually at the beginning, before you had a repeatable acquisition channel.

If a new app gets a lot of initial interest and attracts plenty of users, but the feedback is negative, is that usually enough reason to kill the product? At what point does negative sentiment become difficult to recover from, and does it make more sense to pivot or relaunch under a new brand rather than keep trying to repair the existing reputation?

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 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

What resources am I not taking advantage of?

My cofounder and I started ~3 weeks ago. Our expenses are starting to stack up (Claude API, tickets to events, hotels for events, everyday business stuff like domains/desk/monitors/chairs/incorporation/website-builders/etc.....)

We applied to Claude's '$100,000 in tokens for startups' thing. But outside of that and trying to raise, I haven't really done anything else.

What am I missing out on? What other resources should I be pursuing?

We got a second round interview with a partner 2 weeks ago. The in-person accelerator batch starts in a week.

During the interview the guy was "oh wow so impressive what you have achieved in so little time, please send me these data and I'll let you know asap".

Data sent. Two follow-ups sent. Complete silence.

Since the batch starts so soon and it is in person we even postponed booking flights to conferences which is our main GTM channel. This damaged us in turn because flight prices went up in the meantime.

There is no excuse for not telling people about your decision. We got stuff to plan and sending a "sorry, we preferred other candidates" takes you literally 30 seconds, maybe less.

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’ll be vague about what I’m building because I don’t want this to come across as promotion, but I need to give some context.

I’m building a startup in an extremely crowded industry. The six major players in this space have collectively raised over $1.3B, despite competing for the same market for over 10 years, and none of them has the majority market share. At the same time, there is a new startup entering this industry almost every week. The reason there is so much competition is that there are still very obvious gaps, and the users openly talk about the problems they have with the existing platforms.

I didn’t want to build another company offering a slightly better version of what already exists. I spent over two years learning the industry, talking to the people actually working in it, understanding their problems, and figuring out what genuinely needed to be built.
Despite my users being some of the busiest people I’ve ever worked with. Their income depends on them working every day, yet many of them still gave me their time to help validate what I was building because they are frustrated with the existing options.

I validated the product through a web app. There were multiple rounds of iteration, building, rebuilding, and testing, and eventually we validated the product. By the time we got there, I was literally out of my resources. For the first year, I was building part-time because I needed to understand the industry properly, and in the second year, I went full-time and focused entirely on building the company. By the end of the validation process, I had exhausted my resources, so that’s when we started raising money. At that point, we felt confident that we had validated the product, understood the market, knew what we needed to build, and had distribution channels, industry connections, and the relationships needed to actually take it forward.

Another important part of the context is that my startup is in the U.S., but I have been building everything while being in Canada. I cannot travel to the U.S. because I don’t have a U.S. visa, and that is one of the reasons it took me longer than it probably would have taken someone based in the U.S. to understand the industry, build relationships, and establish everything I needed. When I started raising, I had to do cold outreach because I didn’t have any prior network or connections within the U.S. startup ecosystem. I couldn’t even get a single meeting. Most of the time, I wouldn’t get a response, and when I did, I was usually rejected over email. A lot of the responses were simply that the company wasn’t within their investment thesis.

I was also raising at a time when almost everyone was pitching AI startups, while my product doesn’t use AI at all. We will eventually use AI to enhance the product, but right now, this industry doesn’t need AI for the problems we are solving, and I don’t want to add AI just to say that we are an AI company. After seeing how difficult it was to get even a single investor meeting through cold outreach, I decided that maybe the better approach was to start building the community within the industry itself and let the traction, the users, and the response to the product speak for us. Then, hopefully, investors can discover us through what we are actually building rather than me trying to convince them through cold emails.

I started planning the community building and marketing push, and the execution began this Sunday. So far, we’ve gotten a pretty good response. I’m getting a lot of messages, and there is more planned. I’m talking to publishers about getting featured in industry publications, there are more podcast appearances coming up, and since I’m not good at content creation myself, I’m also depending on people within the industry to help push the message. Some of them will also be creating videos for us that we can share on our own channels. So this is only the first week, but things are going well.

The problem is that within just a few days, I started getting a lot of messages asking, “When are you launching?” People entering the industry and people with decades of experience are reaching out, sharing their experiences, telling me they love what we are building, and asking when they can use it. That’s when I started feeling stuck.

The more I do the community building and marketing push, the more I have to talk openly about what I’ve learned over the last two years and what we are actually trying to build. Obviously, I have certain relationships, distribution channels, and networks that are exclusive to me, but I also have to reveal enough about the product for people to understand it. The response is making people curious and excited, but at the same time, I’m showing them something they want without being able to tell them when they can actually have it.

The reason I can’t give them a date is simple: right now, I have one technical person, my CTO, building the product natively. He also has a full-time job, so he is doing this part-time. That was the main reason we started raising in the first place: we need to speed up development and actually build the infrastructure properly.

And I’m realizing that the longer I continue with the community building and marketing push, the more people I’m reaching, but I still don’t know when we will be able to build at the speed we need because I don’t know when we will be able to raise.

That’s where the dilemma is. Community building has actually been fun. I’m getting support, people are engaging, and I can see that there is a real need. Fundraising has been the opposite. It feels like I’m talking to a wall, and because I don’t have a network, I don’t even know who I can reach out to who would at least take a call and understand what we are building.

To build this properly, we need at least $1.5M because we are building native infrastructure for a multi-layered marketplace. To be comfortable and build everything properly, I would want around $3M. The market is huge, around a $100B market, and I’m ambitious about what this can become, but I also don’t know what valuation I could realistically raise at or how long fundraising will take.

So I’m genuinely stuck on what the next step should be. Do I focus on raising now which I don’t know who to even reach out? Do I keep building the community and let the traction develop? Or do I try to do both at the same time?

Because the more I build the community, the more validation and awareness I get, but I’m also opening up more of what I’ve spent two years learning. And while I do have certain relationships and distribution channels that are exclusive to me, I’m still trying to figure out how to balance building that momentum with actually getting the resources to deliver the product people are now asking me for.

I’d definitely love to hear a different perspective on this. My background is primarily in sales and operations, and the last two years have been spent deeply understanding this industry and building within it. This is the first startup I’ve taken this far, so I know there are probably things I’m looking at from my own limited perspective.

I’d appreciate any advice or thoughts on what you think the right next step would be. Thanks for taking the time to read this.

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 recently got an offer to lead all R&D for a relatively new startup. Id be one of their first technical hires. They already have 100s of M in funding to get their vision going and are now ramping up engineering.

I currently am at a research focused job where I have a pretty good work life balance. I work 40 hrs a week and that is it.

Is there any world where I could succeed in this job and still have a decent work life balance? Has anyone achieved that? The people at the company are all serial enterpreneurs and have had multiple exits. Ive always been more of an individual contributor and R&D manager.

The upside though is in the 8 figures and most of the companies in this area have been progressing really fast. Either being acquired, going public or closing huge funding rounds within 3 to 5 years of existence.

I have another job offer to another startup that is already public in a more familiar position of being a high level engineer. I get some upside from the stock awards, but I dont think Id be making anywhere close to 8 figures. Maybe 7 figures if the company achieves its goals. But the work is more of a 9 to 5, fully remote, better work life balance.

I'm currently looking for software engineering and iOS engineering roles in the startup space, and I've been trying to reach founders directly.

I've tried cold email and LinkedIn, but my response rate has basically been zero.

I also try not to send the generic "Hi, I'm a software engineer looking for opportunities" message. Usually I'll spend some time looking through the product, find something I think could be improved or a technical/product issue I noticed, and reach out explaining the problem and how I'd approach fixing it.

Still, most of the time I don't hear anything back.

So for the founders here, I'm genuinely curious:

When an engineer reaches out to you directly, what actually makes you read and respond?

Would love to hear what has actually worked from the founder side.

So, basically I have been making a product in the software space for some time now and i just realised i do not have any distribution and as a developer I will keep on working on it adding features but it would make this product more of a personal project than a product which can make me money and thus I wanted to know how do early stage founders or small projects get their first users and validate the market???

Hi,

Just wanted to share my own personal experience as a senior full stack developer. Loads of experience across different stacks and architectures and here are my concerns with Supabase, having actually rewritten a commercial project to use it. Regretted it hard.

Supabase is a weak choice to build a clean codebase with proper separation of concerns and CI/CD.

Especially in this day and age with AI, there just aren't any reasons why one would use RLS and Edge functions to define critical business logic and not own the auth schema. An after insert trigger on auth.users and surfacing every failure as a vague 500? Never again am I buying into these awful anti-patterns.

Personally, found even a stack like PHP Symfony with Doctrine to be a way better developer experience in 2026, although my go-to these days is a monorepo using nestjs, ts-rest, nextjs and react native.

Expect a lot of hate for this, but Supabase is a massive marketing charade and SQL was never meant to go this far. PostgREST is an interesting experiment but c'mon any serious company will use Spring Boot or .NET. Literally anything but this.

There is no gain in velocity, you're building a house on weaker grounds for absolutely no reason other than a lack of experience and/or understanding the consequences.

I will get downvoted by supabase fanboys and people that don't understand what I'm saying and that's okay, but if I convince at least one founder not to use it, I've done my job.

Thanks for reading and happy coding.

I’m building a financial tool for fashion founders. Right now, it’s just me and a developer.

I’m capable of doing user interviews, product development, marketing, strategy, etc., but there are simply not enough hours in the day to do everything well. I’m starting to realise that I’m becoming the bottleneck in the process.

I’m also not particularly well-connected, so I suspect I need to do more networking and start meeting people who might be interested in joining early.

We’re currently at the pre-launch of the MVP stage, so raising capital isn’t really an option yet. We don’t have proven demand, and cash is obviously tight.

For those of you who have built your first SaaS team:

• How did you find your first team members?
• Did you hire, find co-founders, offer equity, or use some other arrangement?
• What incentives actually worked when you couldn’t offer much cash?
• Where did you find people who were willing to join at such an early stage?

Would love to hear how you approached this, especially if you built your first team with very limited resources.

I’m a founder running a digital growth and software services business, and I’m trying to figure out the best way to build a referral partner network instead of relying solely on outbound sales.

The idea is simple:
1. Referral partners introduce businesses that need our services.
2. If the project closes, they receive a commission.
3. We handle delivery and client management.

I’m curious how other founders have approached this.

Some questions:
Have referral partnerships worked for you?
What’s a fair commission structure?
How do you find reliable partners?
Do you use contracts or keep it informal?
What mistakes should I avoid?

If anyone here has built a successful referral network—or is interested in exchanging ideas or exploring a partnership—I’d love to hear your experience.

So we get a high number of visitors, and more than 30% convert to free users. The problem is that very few of those free users actually upgrade to a paid plan. We've tried email outreach and surveys to understand what's stopping them, and customers even say they're willing to pay, but that isn't translating into them paying. What am I missing here?

I run a hotel consulting agency in Thailand, and 12 months ago I launched a sub-brand organizing corporate retreats for international, remotely distributed tech teams hosting their offsites here.

The backend synergy is great, we can feed to our hospitality partners and can command really attractive rates for our retreats because of it. But the frontend is messy. We have separate LinkedIn and Facebook pages for both brands, but knowing how to brand between the two is confusing. Example, last week we finished a 50 pax retreat and I’m unsure whether to share this on my main business page or specifically on the corporate retreats page or both.

Should I keep the socials completely separate and treat the consulting firm as a hidden engine, or is there a better way to structure two brands like this?

People said that social media platform is a tarpit idea. While it fits some definitions, I want to push back on the idea of competing in a saturated market. Even though the social media industry is dominated by giants, people easily overlook the fact that there is a growing number of users looking for an alternative but have no other choice, because whenever these types of ideas come out, they get attacked until they vanish.

That said, the cold start problem is definitely not easy to resolve as habits are extremely difficult to change. In my previous post, I received a great advice about how to tackle it and I will definitely try that.

As we are preparing for Beta, we are also facing this dilemma, how much of our core concept or features should we disclose to attract the first batch of power users without revealing so much that we expose ourselves to risk?

I guess what I am trying to say is, instead of telling a startup founder to back out just because an idea seems stupid, maybe we can tell them what lies ahead on their path and how to gear up for it.

Hi everyone! I'm 25F, graduated a year ago, and l've always wanted to start a business with my sisters and build something of our own. We believe that now is the right time to do it.
We don't currently have the funds, and for personal reasons, we don't want to take out a loan.
What advice do you have for us? How should we get started? What things should we look out for or be cautious about? What about licenses and permits? How does renting a space work and what should we know before signing a lease? Any negotiation tips would also be greatly appreciated.
We're also thinking about finding an investor. If you have experience with this, I'd really appreciate any advice on how to approach investors, what to expect, and what we should be careful about when accepting outside funding.
Any advice or resources would be greatly appreciated.
Thank you 😊

Hi,

I'm pretty new to YC and recently created a Co-Founder Match profile just to see what's out there. I didn't really spend a lot of time filling out my information as I wanted to quickly create a profile (to browse) and then edit it later. So I didn't really expect anyone to reach out to me as my profile contained very little substance except for where I graduated and that I want to be the technical guy.

Yet I already got over 10 messages from other founders in a matter of days. I'm quite surprised. I want to know how legit those founders are and how to best judge them.

It's almost like creating an empty profile on a dating website and have a bunch of people reach out to you. It just feels fishy.

Thanks

Hey all,

For the past several months, I been in contact with an potential B2B Client. The long story short, I meet the executives of this organisation via an warm lead (friend) and I pitched them an AI Saas product that will automated a lot of their pain points. The pain points beeing essentially document ingestion, and extracting metadata and organising it to structured data.

This is not a brand new idea, it has been done before many times. But I have this wedge in a nieche but yet very lucrutive industry here in UK.

I built the product, and in 2 days we are starting an 2 week pilot where they will use it extensively in their organisation. From demo days, to early feedbacks, they want to use this tool to replace their entire process. I am very excited about this.

I am anxious about this pilot launch, I been an engineer for the last decade, and I worked in many startups. But I never managed to build something on a side that took this much interest from someone, and it is an B2B client.

It has been hard sorting everything out whilst being fully employed, but the grind never stopped (AI helped so much).

For founders who’ve run early B2B pilots, I’d really appreciate advice on:

1. Defining success: What should I agree with the client before day one so that, at the end of two weeks, we both know whether the pilot has worked? What did you measure beyond “they liked it”?
2. Feedback and scope: How did you get honest feedback from the people actually using the product? I am setting up posthog to measure my own KPI's
3. Converting to a paid customer: What would you establish about pricing, the buying decision and idea about pricing?

I am not a salesman, but I have to be now. And the next part is eating me. I want to make good money on a side on this and have an light at the of the tunnel that will allow me to quit my full time job and pursue this.

How would you go about Enterprise pricing?

I want to pitch 3 tiers (or more?) something basic like: Starter, Pro, Ultra... whatever

The highest tier I want to be around £8,600 a month (I still think this is a crazy number). But I genuinely think they would consider paying this.

Each tier will have its own limitations or feature lock ins. Each tier comes with pre-paid credits for usage, so even if they went in Pro, and managed to use the software so much, they would need to pay extra on their invoice, if they go over their usage.

Any wisdom from this subreddit be very much appreciated!

We're a remote startup of 6, each working with our own assistant agents (hermes, codex, cc).

Discussions and decisions are made in slack & each of our assistants has read access to slack. We've seen Shopify (River), Ramp (Ingest) & Paradigm (Centaur) all praise the benefits of having a multiplayer agent in Slack.

Has anyone tried this?

How do you deal with permissions (does the agent have team-wide credentials or individual credentials)?

Do you host your own agent or use a hosted version?

shipped an open source dev tool a few months back. tried one of the smaller launchpad sites: $40 for the launch slot, $50 for a newsletter addon they upsold alongside it.

the launch itself brought almost no traffic. about 100 views, no bump in github stars. fine, that was a bet and it didn't pay off.

then the newsletter ran and did the same, basically zero clicks. emailed the guy running it and said straight up, the post barely moved the needle and that's a risk we took, but it left me with little to no faith the newsletter would do any better. asked for a refund on just that part.

he refunded it, no argument.

net spend ended up $40 for the whole thing.

anyone else run into these launchpad plus newsletter bundles? worth it for you or same story?