Starting a startup as CTO / Head of Product
After less than a year, Glassbreakers is now a team of 10, we have thousands of active users on our free product, we’ve expanded into enterprises with paying customers and raised over a million in seed funding. After a few of my Glassbreaker matches inquired, I started to reflect on what it’s like to build a startup as a CTO / Head of Product. I wanted to share my journey, advice and insights to others who are starting out as product leaders.
I’ve also started a CTO / Head of Product roundtable within the Bay Area to swap advice and discuss how to succeed, regardless of gender, in this field; sign up here.
Validate your idea has a demand
The day we met, my soon to be cofounder and I were sitting at Arlequin Cafe in Hayes Valley playing the startup game of what problem would you want to solve. After deciding on inequality in the workplace and throwing out ideas, we landed on mentorship.
That weekend, I built a landing page that said “A mentorship community for women” and “Sign up for beta.” My cofounder and I watched the analytics feeling almost confused at how many organic hits we were getting each day to the site. After a couple weeks, we had 1000 women on the waiting list. As a product person who has launched ideas on the side before, I knew we were onto something. When my cofounder went to a meeting with an investor and returned with 5k, we quit our jobs and dived into the crazy, yet wonderful, experience of growing a startup in Silicon Valley.
How to choose your cofounder
I had been meeting with several people in the San Francisco area looking for a cofounder. I moved from Boulder to San Francisco for a job in digital advertising, but knew that I wanted to start a startup ever since I interned at my father’s company during summers when I was in my teens. Here’s what to look for when choosing your cofounder:
Find the yin to your yang — a team of two
Eileen and I have some overlapping skillsets, but my strengths are in product and hers are in finance. I have a wide network of designers and engineers, and Eileen has a wide network of marketing experts. As CEO, she’s pitching all the time and thinking about the evolution of our business model; as CTO, I am envisioning our product roadmap for the next five years and working closely with different types of personalities. I’m laid-back and a thoughtful communicator while Eileen is effusive and hyper-communicative. When people meet us, it’s obvious that the combination of our strengths and differences makes us a successful team.
Getting to that point, however, isn’t easy. Here are some steps we took before diving into the crazy commitment that starting a company together entails.
Have the following conversations upfront
- Decide who will be featured in press releases, interviews and periodicals
- Distribute equity equally — it’s a red flag for investors when co-founders don’t have equal leadership and control
- Ensure you’re both on the board of directors
- Discuss your communication and working styles, and make sure to set clear boundaries
For example, I had to explain that each time I’m interrupted it takes me 10–20 minutes to get back to where I was in solving a code problem. This is a new concept to those who haven’t worked with designers, engineers or writers before.
Don’t hold it in
The co-founder relationship is more complicated than most romantic relationships. I’m the type of person who gives instant feedback. I hate holding onto things and becoming resentful.
At first, it might have been a bit jarring to my cofounder to get such honest feedback, but I found that it created a higher level of trust. Honesty makes it easy to clear the air, figure out the why and help each other implement change. In the beginning, we gave one another the benefit of the doubt and learned to trust that we both have the same end goal. Giving constructive criticism right away was key in enforcing to one another our underlying intention was to make Glassbreakers the biggest success ever. Starting a company is difficult for reasons one might not expect. It’s not the fundraising, long hours or the demand to scale quickly, it’s the complexity of interpersonal relationships under pressure.
Create something for a greater cause
After attending Summit at Sea and watching a panel on social impact investing, I believe that it will be standard for companies to have both strong business models and social impact goals (just think of fast-growing companies like Tom’s, Warby Parker). With new financial structures being put into place like social impact bonds, there will be more capital to support these innovative ideas. Regardless of the economics, it makes a passionate bond between my cofounder and teammates that is bigger than ourselves, which is a unionizing force.
How to manage your schedule those first months
It was the best of times, it was the worst of times. This was a really exciting time in my life because I would wake up and have an entire day to create. On the other hand, I was the only engineer and all of the pressure was on me.
There were times I felt lonely working from home without a team (I played Netflix movies in the background) and my emotions were a rollercoaster from fundraising updates. There’s also a lot of ups and downs about the tradeoffs you need to make between creating prototypes, designing decks, testing with users and building the MVP of the product. At the beginning, done is better than perfect, which is hard because you want it to be perfect so badly. All in all, it got the company where it needed to be and my calendar is more dynamic since we now have a full-time product team. Yay!
Monday — Friday
- Wake up around 6 or 7am: Drink coffee, eat breakfast, review analytics and read user feedback
- Lunch: run or yoga and eat
- Code or design research from 1–7pm
- Get update from cofounder on fundraising or sales
- Cook and eat dinner with my fiancé, which we mainly discuss software architecture and implementation
- Respond to around 100+ emails / day
- Try to unwind with tv or fantasy books
- Sleep / lie awake thinking about the product and fundraising or just get up and code for a few more hours
- Spend time in nature / hiking
- Read the physical New York Times and respond to emails
- Meet product-minded folks at 10 or 11am for a day of whiteboarding
- Determine needs for the week
- Call, walk or grab a coffee in Hayes Valley with cofounder for a huge catch up and goal setting
- Understand your personal limits and create routine around them. For me, I need to spend Saturday hiking with my fiancé or friends and to be in nature.
- Get healthcare for your employees. From coding too much without blinking while wearing contacts, I ripped my cornea and had to seek medical help. Getting healthcare for our employees was our first priority — while working long hours things tend to happen both physically and mentally.
- Avoid burn out. I’ve seen quite a few other CTOs and cofounders don’t do too well from trying to keep a similar schedule while smashing Red Bulls and taking lots of unprescribed Adderall. Most of the CTOs end up burning out, their families intervene and you might doing irreversible harm to yourself. If you feel like you need to do this to be a founder, question if you’re ready.
- Eat healthy. I followed the Whole 30 eating plan and was the sharpest I had ever been in my life.
What to do If you run out of money
I put everything into Glassbreakers and wasn’t getting paid for a long time. Even now, my cofounder and I have the lowest salaries because we want to put everything back into the company rather than our personal bank accounts. In the long term, our shares will pay off; in the short term, you might run into some problems.
- Find a project you can jump in and out of quickly that pays for the amount of time you need for your personal runway
- Choose a relevant project so it is still furthering the value of your skills and company
- Plan for the space you need to complete the work and coordinate with your cofounder
When I almost ran out of money, I joined a project where I helped build an algorithm with a Stanford software engineering PhD and the associated consumer-facing site. I completed it in 12–15 days, was able to live off of that side project for almost 3 months, and felt more confident in my ability with algorithms.
How to transition from an individual contributor to the leader
The day will come when your company’s budget has room to make hires and you can also pay yourself! It’s an odd mix of learning to let go of control, realizing there are always more holes to fill once others are filled and holding back from diving into every detail. Here were the hiring and structure practices I set up early on, which has been successful thus far.
- Do a phone pre-screen and make sure you’re aligned with the same goals — this will save a lot of time.
- Spend an entire day together in the office. It’s hard to gather what it would be like to work with someone from an hour or two, so have them come in for the day and spend a lot of time pairing on either design or code.
- Don’t act too desperate. A few times I asked engineers to join after a full-day interview; this always turned product people off, so I learned to wait a day or two more to really think about it. (Tends to be the complete opposite with sales hires.)
- If you’re not sure, ask them to do a paid trial period. It’s worth it to yourself, the candidate and your entire team to do a trial period if something isn’t sitting right in your gut.
- Take bias out of the process. We gave a design challenge to 8 potential employees and removed their names from the final output; we then chose which one we liked the most solely based on the work.
- Tap your network. By working with people you have worked with before, the above process is much quicker.
Put together your product team’s principles
- Features need to be user experience tested. If we are disagreeing about a feature set, it’s a waste of our time because we should just ask our users.
- Everyone is in “The Forge.” In past jobs I was always frustrated by being pigeon-holed into a user experience designer or software engineer role when I was passionate about both. I nicknamed our product team “The Forge” with the ethos that everyone contribute to any step of the process.
- TDD. Great code isn’t great unless it’s tested. Our test suite cover 97% of the product!
- It’s not about butts in seats and face time — it’s about getting it done. Flexible schedules are key into making this happen. Not everyone is focused or productive from 9–5 in an office, so don’t make them be!
- Mobile first.
Create structure that allows for awareness and constructive criticism
- Remote daily standups in Slack
- Monday AM = weekly goals and priorities with everyone for the week
- Friday = retro on how the week went
- 1–1s every other week. This is an easy space for everyone to talk about how they are doing and to see if there’s anything they need that you can provide (i.e. mentorship, work from home day, goal setting, etc.)
- Monthly checkins and retros aligned with product roadmap
- Give space to air what’s going wrong. During any of these meetings, except for the daily standup, there’s room for negativity. I found in the beginning of our retros, no one wanted to be the person who said something went poorly that week. This was detrimental at first, because we needed to air our frustrations and figure out how we could make things better. I would always encourage everyone to discuss the negative which has led to a more open and relaxed environment. If someone didn’t want to discuss something in a group, there was always our 1–1s every other week to talk there as well.
Get advice from the best
We have amazing investors in Glassbreakers (70% women). When I started hiring, I reached out to hear from three key players. The best advice that I’ve applied to working with the team is the following:
- Mitali Pattnaik: As a manager, it’s important to set up long swimming lanes for each person. You don’t want them to feel stuck like they have to ask you questions along the way — provide them everything they need to keep moving as fast or slow as they need to.
- Sara Haider: Have fun when things are good and celebrate milestones. It’s awkward when things start to go poorly and then companies begin to have outings.
- April Underwood: Hang up your mission in the office for everyone to see as a reminder of what everyone is working towards.
Learning, doing something different every day, feeling a rollercoaster of emotions, working with highly motivated people, meeting inspiring voices of our generation, making a difference, celebrating victories, working through downturns and, day by day, improving your product for your users and yourself — that’s running a startup. New challenges arise quickly and you have to be quick on your feet to pivot. I love the ride and, if this sounds exciting to you, then nothing should hold you back from being a successful CTO / Head of Product.
Would love any feedback on this article or to hear from others about how they’re approaching their experience! @laurenmosenthal