Office Hours: I'm the COO of a Series B fin tech startup. I'm Holly Grant.Featured

Hi everyone!I’m the Chief Operating Officer at LTSE. We are a mission-based, fintech startup that supports companies at every stage to operate with more of a long-term focus. Our work ranges from enterprise SaaS to the imminent launch of Long-Term Stock Exchange, the newest SEC-approved stock exchange in the United States. I joined LTSE as Chief of Staff and one of the first five employees. Over my four-year tenure, I have taken on roles as Head of Finance and Operations and VP Operations. I have helped close our Series A and Series B financings and scale our team. In my current role as COO, I manage our executives and lead the cross-functional team that is responsible for finance, legal, people ops/HR, talent, administration, and culture. I started my career in the family office world, supporting a serial entrepreneur in running and investing in a number of businesses. That experience exposed me to different industries and teams and informed my perspective as an operator. I have a BA in Foreign Affairs from the University of Virginia and live in Brooklyn, NY, with my partner Ryan.Ask me anything about the role of Chief of Staff or COO at a startup, my tricks for being successful at an early stage startup, raising venture capital, working in fintech, or any of my personal hobbies--well being, mindfulness, fitness/movement, travel and personal finance.Lastly, we are actively hiring right now at LTSE, so if you are interested in learning about new opportunities please check out our open roles.
Thanks so much for joining us @hollygrant!Elphas – please ask Holly your questions by this Friday. She may not have time to answer them all, so please emoji upvote the ones you're most interested in reading about. Thanks!
Hi Holly - would love to better understand what you found most surprising about the COO role/Chief of Staff role? And how you first found and honed your interest and skills in an operation/execution oriented role?
Hi Jessica!The thing I have found most surprising is that success in both roles ultimately comes down to coaching people on how to unblock themselves (and each other) and a willingness to have hard (kind) conversations. I’m a big fan of Brene Brown’s work, and I try to live by the motto, “clear is kind.” In terms of discovering my interests and skills, I’ve used reading, online courses/communities, personality tests, intuition, and trial and error. I’ve taken Myers Briggs, Strengthsfinder, and Enneagram to gain a better understanding of my personality (although I don’t take any one test as the single source of truth). I’ve also polled friends and colleagues on their views of my strengths and worked with coaches who are willing to give me candid, frequent feedback. I subscribe to the belief that we are most effective when we cultivate our strengths and build teams that complement us. I try to pay attention to the kinds of activities that give me the most energy because that is often a sign that we are working from our strengths.
Wonderful, thank you so much, Holly :)
Welcome Holly! 🙌Awesome background. Here are some of my questions:1. Working for companies with fewer than 10 people at its very early stages means one might have to be a jack-of-all-trades. It sounds like you also wore many hats over the last 4 years. I'd like to hear the tricks and skills needed to be successful at early age startups. 2. When raising funds between Series A and Series B, were there significant changes, differences, or expectations from investors or the team itself? 3. Regarding your personal hobby around personal finance: any thoughts on dividend stocks or ETFs? Good? Bad? Depends? Thank you very much in advance!
Hi Weiting!1. Yes, I find early stage company-building to be more about mindset and less about expertise. Individuals who thrive in early stage environments have a willingness to try things, own things, move with a sense of urgency, and (honestly) evaluate the efficacy of their work. I use "willingness" deliberately because I believe these qualities can be learned. Uncertainty is rampant in early stage environments, and we, as human beings, do not have the best relationship with uncertainty. However, I believe that if we're willing to train in getting more comfortable with uncertainty, then we can develop a superpower of sorts and be much more effective on early teams (and beyond). That training can take many forms. At LTSE, we use the Lean Startup methodology to manage uncertainty, which helps us be precise about the assumptions we're making and the signals we're looking for from customers. I also lean on mindfulness techniques. Common failure modes I see include perfectionism, over-planning/over-researching, and attachment to specific strategies or outcomes. I definitely struggled with the perfectionism bit in the early days and continue to work on letting that go. In summary, I view early stage company-building as a great exercise in surrender. 2. There was definitely a shift from Series A to Series B. The stakes got higher for us and for our investors. We needed to show that we had used the story and initial funding to create enough traction to put ourselves on a path to a highly lucrative business. We were lucky to have the same lead investor in both rounds.3. As with all things personal finance, it depends. :) I'm a big fan of defaulting to the S&P500 because it's simple and tends to outperform most managed funds over time.
@hollygrantHello Holly,I hope you're doing well.Thanks for doing the Office Hours!2 Questions1 What are tips for managing imposter syndrome?2 What is your go to motivational song?Thank you.Warm Regards,Ekua
Hi Ekua!1. To manage my imposter syndrome, I invest in daily self-care practices (e.g. exercise, healthy food, sleep, connection with loved ones, meditation), cultivate my own spiritual life, practice self compassion, seek out inspiring examples of people who are "in the arena", and fact-check my own self-criticism. I have built a support team, and I am diligent about asking for help when I need it. Would love to hear your tips too!2. Beyonce’s entire Homecoming album!
@hollygrantThanks so much for your response. I have realised that I struggle with self care practices and I am working on embedding, committing and giving myself permission to have down time. I've just recently committed to "Friday Ekua time" every week during "work time". In terms of tackling "imposter syndrome", I have to say, "Yessssss and high five to" what you said " fact-check my own self-criticism". I have a phase which I use with my clients and its this "FACTS are Friends". Which I ask them and myself to ask, is my "negative thought" really a fact? Is there any evidence that what I think is true? When the answer comes back as "No", I'm like we have our answer! It's so easy to let these thoughts take root.I recomend and I think I need to do what I said in my own recent blog, which was to do a "spring clean" of my own personal negative thoughts! I think, I need to take my own advice! Lol. Here's the link to that blog: top tips for managing "imposter syndrome" would be:Practice daily positive affirmationsRegularly "spring clean" your mind of negative thoughtsFact Check your negative thoughts and beliefs Celebrate your success regularly Thanks, for making me think about my own practice.
Hey Holly thank you for giving us your time :D My question is when are you truly ready to take up leadership role in a start up? I work as a Data Scientist at a Fortune 500 FinTech company and I recently turned down an offer at a startup to lead as a Director of Data Science because I felt I wasn't ready. Director at a fortune 500 is a old white male, seasoned with years of experience.. and that's what I have been exposed too. How do I take the leap and be OK with what I know? or be prepared? so that I am ready when the opportunity knocks on the door.
Hi Shweta! In reading your post, "start before you're ready" flashed through my mind. :)Some questions for you to consider: - Startups and Fortune 500 companies are very different environments. What skills do you need to be an effective Director of Data Science at a startup? Be as specific as possible (fear has a way of moving the goal post). In my humble opinion, a lot of startup learning happens on the job. - If you were to step into this leadership position, are there mentors or other practitioners you could enlist as advisors (even on an informal basis) to coach you through the harder moments? (Some of my best advisors are people I'm not even in personal relationship with but make their body of work public and influence how I show up to do my job. )- Can you trust yourself to ask for help if you are in over your head?
This is great advice @hollygrant!! Thank you for taking the time to write this :D Also I added "Start before you're ready" to my reading list!I completely agree that I need to be specific, which is where I struggle the most, if I am not focused on a target, I will keep firing in all directions (which I pretty much feel I am doing). I am also currently building a network to learn from as many people as I can who have been in the field of my interest and succeeded. The last point got me thinking, its about trust and fear. Its easy to ask somebody you know very well for advice, but reaching out to people outside and asking for help without constantly thinking "what do I have to offer?" is difficult.
Hi Holly!Would love to find out about your role as a Chief of Staff. I'm currently thinking about my next step after starting my career in consultancy and the idea of a COS role appeals to me. What would you say is the amount of years of experience needed to land such a role and what are they key learnings and challenging you faced as a Chief of Staff?And a final question. What motivated you to join the LTSE and what keeps you there 4 years later?
Hi Asta!Chief of Staff is an amazing role because you get to experience the breadth and depth of what it takes to run a business. I have found that the role varies significantly based on the stage of the company and the needs/preferences of the executive (or team) you’re supporting. For that reason, I’ve seen Chiefs of Staff be successful with anywhere from 2-10+ years of experience.There are certain traits that will serve you regardless of the stage or an executive’s preferences: the ability to build and maintain trust with a diverse range of stakeholders, having a strong customer service orientation (i.e. understanding needs and solving problems), making things happen, and being an excellent written and verbal communicator. The last thing I’ll say is Chief of Staff can be a lonely job because you see/handle a lot and the role requires you to hold everything in strict confidence. For that reason, I found it critical to have solid self care practices and support structures in order to do the job well. Three things moved me to take the opportunity at LTSE: 1. Mission - given my love of personal finance, I saw the systemic impact LTSE could have by creating access to high quality investments for retail (individual) investors. 2. Quality of the team - the early team was mature and had deep expertise. I knew I had a lot to learn from them (and this is still true today as we grow our team). 3. Opportunity to practice Lean Startup - I followed Lean Startup in my family office job, but I didn’t practice it. I figured the best way to learn the methodology was to work with the creator himself. It has changed how I think and problem solve.
Hi Holly - thanks for answering our questions!I’m curious about what startups (both ones you’ve invested in and ones you’ve worked at) look for in candidates for ops lead roles. Particular experience? Professional and personal characteristics? Network? My medium-long term ambition is COO at a startup, and am presently thinking through my next career step, so any insight appreciated! Thank you again.
Hi Claudia! I am happy to give you a quick read on the importance of each category you mentioned for an Ops Lead role:- Particular experience: Heavily weighted. I'd be looking for evidence of your ownership and management of a strategic initiative or product. - Professional and personal characteristics: Heavily weighted. Personal qualities I value for this role (and all roles): reliable, resilient, candid, and trustworthy. Professional qualities I value for this role: talented communicator, makes things happen, rigorous, collaborative, systems-thinker, and analytical. - Network: Not a factor.
Hi Holly,LTSE sounds great! The market definitely needs long-term thinking!From the early days at LTSE, do you have any insights into how the team approached building your brand and marketing? I'm working with a pre-seed fintech startup. Given that we're pre-seed, I'm leaning towards low and no-cost marketing options for now (Squarespace, etc.) and to hire a graphics/brand consultant later once we have funding/revenue. Thanks for taking our questions!
Hi Holly, I'm a Tech Recruiter in the startup space - I'm currently assessing a variety of companies between Series A and C. I'd love to hear about your experiences with headcount growth and how that informs your decisions now when deciding how much to grow by and why.