Why I am joining Unusual Ventures as an Operator in Residence

My career thus far has been a series of transitions from large companies to smaller startups, and this move is a natural progression. In order to explain exactly why I made this decision, it's important to know a bit about my journey and how it culminates in joining Unusual Ventures as their first Operator in Residence.

I began my career in the Sales Engineering Graduate Academy at the 100k+ employee German software company, SAP. They provided great training, mentorship, and a crash course in how businesses work and how enterprises operate. I also developed a strong network of close friends who sell, manage, and lead at top tech companies to learn from and trade ideas with.

Eventually, I realized that I wanted to own a sales process. I decided to go to Square (800 employees when I joined) to get true experience running deals as an Account Executive. Throughout my time at Square, I was exposed to a high volume of deals, sales enablement, sales operations, management, product marketing, and great leadership. I met great colleagues whom I've remained close with and continue to learn from, and trade notes with such as: Andrew Berger (VP-Sales at Front), Natalie Yatsko (RVP at Pendo), Doug Schuessler (CRO at Resy), Ross Wiethoff (sales advisor at Sweat Equity) among others.

When I met Matin Matovosate and Ravi Parikh who had just started Heap, I knew right away that I wanted to bet on both them and the trends they were riding. As their 6th employee and first non-technical hire, they decided to take a bet on me as well! I left six years later as VP of Sales with revenues in $X0m million ARR, $100m+ raised, and ~250 employees. Growing up at Heap, I crafted my own leadership and execution style with the help of extremely?smart co-workers and mentors. I learned so much about GTM by joining experts in the trenches such as: Neal George, Jim Herbold (advisor), Ken Fine, Dennis Dresser, Lynn Girotto, and Scott Davis (advisor).?

Operator in Residence at Unusual Ventures

It’s commonplace for venture firms to have an Entrepreneur in Residence (EIR) program, where people with largely technical backgrounds (engineering, product, former founders, etc.) can incubate ideas, help portfolio companies, and get involved with the investment process for a few quarters before deciding on their next move.?

Unusual Ventures focuses heavily on the Go-To-Market side of company building and has full time operators in sales, marketing, education, and community that work directly with their portfolio companies. Their Operator in Residence (OIR) program allows experts in these areas to join Unusual for a few quarters to create a similar impact. This way, Unusual’s portfolio companies get to work with GTM subject matter experts as they build their companies, and OIRs get to experience what being on the other side of the fence at a VC firm is like.?

I ultimately decided to take the OIR role for 3 reasons:

1. It is the most fun and rewarding for me to work with $0-10m companies and this opportunity gives me a chance to do it many times over
2. Fits my career aspirations, unique skill sets, and experience
3. I believe and align with UV's thesis and approach in working alongside founders in the trenches to help them reach their goals

Most fun and rewarding working with companies from $0-10m ARR

When Heap was in its infancy, I vividly remember how much of a rush it was to close the first few real deals. There was not only a sense of surprise, "Ravi, this is actually working..." but it also materially moved the needle for the company. It was common for a specific deal to make the company grow 20-30% MoM.

In addition to individual deals and the frequent "biggest deal in company history," the ability to hire great talent at this stage has an outsized impact on the business. I remember hiring Becca Lindquist (now Head of Sales at DBT/Fishtown) and immediately saw her ideas drive up ACV and dramatically increase win rates. I love to see the impact a multiplier can have on the success of the business.

When I reflect on my time at Square prior to Heap, I was most energized working cross-functionally. I was stimulated the most when I was involved with product and marketing on pricing, positioning, testing, and selling new products. I realize that I love launching a product to the market. At this stage, it is imperative to touch other parts of the business, whether it's writing content, producing marketing decks, handling contracts, or running an event. Being a part of all of these functions is not only fun, it also helps you understand the entire business at a deep level.

Over the course of my time at Heap, I had the opportunity to invest in and advise a few Seed stage companies. Working with early stage founders such as Carlo Candella (Sameplan, acquired by Outreach), George Carollo (Dover), and Vikas Murelli (Offsight), I realized that advising companies is as rewarding as building them yourself. Founders can learn from my prior mistakes and avoid roadblocks that may set them back months, or take key learnings that accelerate their growth by the same margin. I am excited to do more of this.

Fits my career aspirations, unique skill sets, and ability to continue learning quickly

When SaaS operating veteran Ken Fine was onboarding as the COO at Heap (now CEO), he helped me realize that my skill set aligns more to a GM or COO than a “plug and play” sales leader. My abilities are uniquely helpful for early stage companies where roles are more nebulous. It will be imperative to help spot risks and opportunities in adjacent functions outside of sales to help the UV portfolio companies succeed quickly.

After the chance to study folks like Ken Fine and other mentors, I've found that you learn the most by a combination of watching and listening to experienced leaders and from getting your hands dirty and doing the work. I expect to get both in this role -- doing the work side by side with ambitious founders and learning from other GTM experts on the Unusual Ventures team that have seen success at companies like Okta, MongoDB, AppDynamics, Amplitude, and Sumo Logic.

In addition to the network I can learn from, a big benefit of this opportunity for me is to dramatically increase the number of Seed/Series A stage companies I see at an intimate level. This will allow me to begin to pattern match, recognize trends, and understand what separates the best early stage companies from the pack. I eventually want to join one company again very early or start my own company and believe this experience will be invaluable.

I believe and align with Unusual Ventures’ approach

In addition to the talent on the GTM team above, I was first introduced to the leadership at Unusual Ventures because I heard founder Jyoti Bansal speak about his experience as the founder of AppDynamics at a Menlo Ventures event in ~2017. I liked the way he was super humble, emphasized delegation, and talked about the social benefits rapidly growing companies can have on large groups of people. The opportunity to join a firm with his ethos engrained is super exciting.

The other founder, John Vronis, is also someone I am excited to learn from and work with. He has been at the forefront of cloud and SaaS investing and is one of the brightest to do it in Enterprise B2B tech. After a few calls with him, I liked his forward-thinking, principles-first approach to subjects folks have often told me can’t be changed. He also has a clear thesis on exactly why Unusual Ventures was created and whom they are set out to help. If you listen to him on this Techcrunch podcast, you can hear first-hand why he thinks most founders getting seed money are getting the wrong help and ultimately set up to fail.

I wholeheartedly agree with their focus to get deeply involved with founders at early stages in the areas where they need help the most: Hiring, sales, product, etc. I am also 100% onboard with early investments in Education and Community in addition to standard GTM functions (sales/marketing/hiring) as the modern GTM playbook. I know how valuable this would have been when we were trying to figure it out at Heap.

Finally, they choose to work with LPs with a purpose. Unusual Venture's success means that hospitals, HBCUs, and other educational institutions will have more funding to create better outcomes for their constituents and the world.

What now?

I am looking forward to “getting in the boat” with the next wave of great B2B Enterprise founders. I am eager to partner with early stage operators and help them mature their skillsets, product, and ultimately increase the likelihood of winning their markets.?

If you want to learn more about UV, the Get-Ahead Platform (GAP), or want tactical advice as an early stage operator check out our content here. And please let me know if there are any topics about which you would like to learn more.?