From the Collective

Meet Operator Collective’s Investing Partner, Haley Daiber Brannan

Caroline Caswell

Haley Daiber Brannan and OpCo Founder and CEO Mallun Yen first got to know each other five years ago when Haley was an investor at Unusual Ventures. As a founding investment team member, Haley sourced and supported enterprise investments like CoScreen (ACQ: DDOG),, and Vivun. She was most recently focused on revenue ops & intelligence, go-to-market strategy, and product education & customer training as VP of Business Operations at during a critical growth period. She was a key leader as the company scaled to new heights - tripling ARR, the team, and the customer base, leading up to a $50M Series C last year. Haley joined the OpCo team in January - read on for more about Haley and why she’s uniquely suited to make an impact at OpCo: 

Tell us a bit about your background! 

I grew up in a small town in Texas about 40 minutes north of Austin. At the time it was a one high school, one Wal-mart, and a Chili’s size of town, but has since exploded along with the rest of central Texas! Being so close to Austin, I’ve been a Texas Longhorn since childhood, so it wasn’t a hard decision to attend the University of Texas upon graduation. What was hard was trying to decide on a “career” at 19 - ha! The pragmatist in me decided that I couldn’t go wrong with accounting - solid job prospects, understanding financial statements could only be helpful, and UT happened to have the #1 accounting program with the ability to get your Master’s and CPA with one additional year of school. I started my career as a financial statement auditor at Ernst & Young (EY) in Austin, focused mostly on public companies in the semiconductor industry. 

From there the road gets a lot more windy! Co-founding a startup with my mom that began as a side project and ended in a pitch to celebrities on a Shark-tank style television show ( what?!), going back to school full-time to pursue an MBA at Harvard Business School, joining a startup venture capital firm right as it was launching, and then switching back to the startup side to join All while moving cross-country a handful of times and doing long-distance with my husband for a few years - a journey in itself!

Where did your passion for startups come from? 

I’ve been drawn to startups since my first internship at EY, where my first client was one of the original venture capital firms in Austin. My task was to research all of the startups in the firm’s portfolio to provide a summary of what the companies actually did ( ironic example of a now perfect task for chatGPT!), and I couldn’t shake the curiosity and excitement surrounding these companies and entrepreneurs. 

With that spark in my head, I was constantly thinking about all the problems I was facing day to day, and how to solve them. My mom is a big inspiration to me, and very entrepreneurial herself, and one idea we both couldn’t shake was frustration that LinkedIn did not serve the purpose that we needed it for - organizing our connections based on how we actually remember people! When we met them, where we met them, through whom we met them, and on and on - NOT by searching for their name. Create an app, how hard could that be right? We started Forget-Me-Not knowing we were destined for greatness! Fast forward… MANY lessons learned, including that it is that hard, and there are countless reasons why there are only a handful of successful social networks. A good idea does not a good company make. But there was no turning back from the startup world - the energy, optimism, ambition surrounding early stage companies was too much fun.

What was the jump from investing to operating like? 

Refreshing and eye-opening! As an investor or advisor, there’s only so much you can do to affect change at a portfolio company. We do all we can to be helpful and provide guidance, and roll up our sleeves and dig in where feasible, but there’s a ceiling. On the operating side, you are seeing an immediate impact of your work pushing the company forward on a daily basis - almost every decision (or lack of decision) has ramifications. Working with and building a team is also so rewarding - you’re all on the rollercoaster together. There’s also a lot of noise in the venture capital ecosystem, taking time to really focus just on execution of shorter term goals was a welcomed change.

You were a key leader during a period of critical growth at - what were some of the operating challenges you experienced and biggest lessons you learned? 

As the company and team scales, things are going to start breaking all over the place. That’s ok and normal, but the biggest challenge is to recognize it quickly, acknowledge it widely, and make fast changes. There’s an inherent nostalgia with the “early days” of startups - so it’s easier said than done to part ways with a process or team-building activity that’s considered tradition.

One thing that “broke” many times that we had to keep re-inventing was our go-to-market model and reporting of the key metrics. As the business grows, the GTM gets more complex - attribution gets trickier, performance of AE’s starts to vary more widely, market dynamics like competition and sales cycle change. The spreadsheet + poorly filled out CRM that you use as a Seed/Series A company to manage your pipeline and the monthly “Marketing Metrics” meeting where you report on MQLs isn’t going to cut it for the next phase.

What inspired the jump back to investing, and why OpCo? 

Mallun inspired me! But really, she is a force. I loved my time operating, but there were aspects that I missed about investing and especially working with companies at the earliest stage. When I was heads down on the operating side, I was just that - heads down. I was really focused on day to day execution and addressing the newest thing that was breaking. What drew me to in the first place was an investment thesis I had been working on around data discovery - how data scientists were still struggling to find and understand the right data sets. The broader view of the big problems that lots of companies/people/departments are facing and the innovative tech breakthroughs that drive solutions was the 30,000 foot vantage point I missed.

One thing that I won’t compromise on at this stage of my career is being surrounded by good humans that make me smile - people that inspire me to want to work incredibly hard because they are just that awesome. I knew Mallun for years before joining Operator Collective full-time, and everyone that I continued to meet in OpCo’s orbit gave me full confidence that these wonderful humans would fit that criteria! And it was also Operator Collective’s model - venture firms have tried many times over to figure out a scalable way to really meaningfully support portfolio companies, often failing to deliver. OpCo truly has figured out a system that works, and the opportunity to continue to learn from amazing operators in this community was definitely one I could not pass up.

How has your operating experience changed your investing perspective? 

When was raising its most recent round, I was head of finance and very involved in the process, given my investing background. It is 1000x easier to ask a bunch of questions than to try and anticipate what questions investors will ask and prepare a pretty data room. So first, just a LOT more respect for the immense work the fundraising process entails on the other side.

There are also a lot of questions that investors didn’t ask, that I was surprised by now knowing so well what things have such a big impact on day to day company building. One area that I always drill into more now when evaluating companies are the decision making processes - how do you set goals? Do you use an OKR system? How is feedback from sales looped back to product & eng? The questions differ depending on stage of the company, but a lot more center around the HOW along with the WHO. As the company grows, so many of the key decisions and keys to success depend on not just the founders, but the people supporting them.

What do you think has changed about venture since you started out? 

I was joking the other day with our team that I actually missed a lot of the wild times! I left venture in May 2020 - so I was on the operating side during the historic highs (valuation, dollars, number of deals) of 2021. Coming back in January of this year, the broader market dynamics actually resemble more of when I started investing in 2017, with the glaring exception of generative AI. In some ways, that area is totally new in terms of really world-changing tech, but in other ways resembles areas I was focused on back then too - one of the first investments we made at the prior firm I was at was a company focused on solving the complexities of putting machine learning models into production.

I do think there’s a lot more openness to new venture models like Operator Collective, and investing via Zoom is definitely a big change from when I started in venture! But a welcomed change that’s here to stay.

What areas are you focused on right now, and what are you most excited about? 

I am excited about all the evolutions in AI. Beyond the hype, I’m excited about use-case specific companies leveraging AI. One thing that I appreciate so much more now after being on the operating side is how specific the business problem that you’re solving as a company really needs to be. It’s something everyone “knows” but in practice is incredibly hard - constantly trying to find the right balance between specificity and measurable ROI for a particular buyer or user vs. not limiting your current addressable market. In today’s uncertain macro environment, large companies with budget must see quantifiable value, and small companies are pulling back on investment in tooling overall, making B2B go-to-markets challenging. 

For 5+ years, Gartner has been widely cited for their prediction that 85% of investments in AI fail to deliver the desired outcomes. I believe this dynamic is changing, as the key developments with some of the recent evolutions in generative AI are totally new user interfaces and the ease of incorporating base models into existing products and workflows. A perfect example of this is our own portfolio company Forethought. These evolutions are making time to value much faster and more concrete for companies investing in AI.

What was one of your first jobs and what’s one big lesson you learned? 

My first job was in retail at a clothing store at the outlet mall. I think one of the biggest lessons I learned was that a smile goes a long way! In sales, finding that balance of being persistent but not pushy is tricky. General friendliness paired with genuine interest can take you far!

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