The Most Surprising Things I Learned Moving From Venture Capital to Startups

Last year, I left VC to become an operator again. I reflected on what I was most surprised and challenged by and what I took away:

From external to internal work

In VC, especially at a high volume seed fund (an early stage fund that made tons of investments each year), I was spending most of my workdays taking external calls with founders, other investors, portfolio companies, experts, limited partners, and portfolio services companies. Most days, I was doing between 15 and 20 calls! Naturally, some of these people I would only ever meet once or a few times a year or just once a month. When we connected, it was largely to talk about a particular topic that would be resolved in the span of the conversation (or at most a few follow up emails after). In the operator world, most of my day is spent heads down working on projects with just a few calls each day largely with my closest collaborators. Instead of just sharing information (as I would in VC when for example catching up with an investor to share deal flow), we are responsible for key deliverables collectively, which certainly represents a very different style of collaboration. In transitioning to greater cross functional work, I have learned:

Share your process. When you are collaborating on something or working on a product that impacts other people, articulate your process and intended workflow. While your work streams may be operatively entirely separate, anyone who is affected by your work or work product can provide valuable feedback, catching possible errors or lapses before they happen.

Moreover, if the other party feels they were consulted and their perspective was incorporated in your process, they will be authentically enrolled in your project’s success. While you may still be the point person on it, others are incentivized to support your project to fruition. If unforeseen obstacles arise, they will approach the issue with an intention of collaboration rather than mistrust.

Touch it once. Of course larger projects should be done thoughtfully over a reasonable period of time, but for small and quick asks like sending a Slack message, sharing a document, adding something to the meeting agenda, fixing a small typo in a deck, responding yes or no to a quick email, or creating a calendar invite, do it immediately. We all overestimate our own memories and inevitably forget some of what we are told to do if we wait for too long. Have a mentality of “touch it once.” Take action on the small tasks as soon as you have a minute and as soon as they arise. By addressing these small but crucial issues immediately, you never let them pile up, and you never let them fall through the cracks.

Make people’s lives easier. In a similar vein, the small things really do add up. People appreciate those who make their lives easier, and being able to do this is an incredibly underrated skill. Send calendar invites as soon as you agree to have a meeting. Add the high level topics to be discussed to the calendar invite title. When you need someone else’s feedback on something, make a Slack group to discuss. On calls when you are doing less of the talking, take notes. Create agendas for each meeting you have. For calls you play a meaningful role in, help people context switch at the start by setting the context and reiterating the agenda.

Become an expert on something. Inevitably, there are many things I am not able to be the expert on, but nonetheless, there are key comparative advantages I realized I could double down on. For example, I am one of the biggest users of our CRM tools. I spent hours watching tutorials, meeting with our customer service manager, and experimenting. After this upfront work, I was able to not only swiftly complete my projects but also help others as well. Similarly, I became one of the primary people to interface with one of our key personas who provided crucial insight for our product and go to market strategy. I jumped on the opportunity and spearheaded related efforts, such as creating sales collateral for this persona and became the go to person in the company to understand the behavior of this prospect type.

Over communicate. Especially in the remote work world, communication is crucial. When someone asks you a question or assigns you a project, it may of course take some time (hours or days) to complete it, but you should acknowledge their request right away and let them know you are working on it and get aligned on the expected timeframe for completion. Nothing is worse or more destructive and confusing than silence.

Tailor your approach. Get to know people’s workload and workflow (you can sometimes see through Trello boards, for example). Are there particular weeks they are especially busy and cannot take on more work? What are their priorities and KPIs? How does your collaboration fit into their priority stack? What is their work style? What are their strengths and weaknesses? Ask yourself these questions before working with others. Structure your collaboration to suit their schedule, demonstrate the value to their department, and assign them tasks that leverage their skill set.

Give positive feedback. Feedback is often associated with criticism. While it is of course important to note and address issues as they arise, let your colleagues know when they are doing something great too. Even outside of a “thank you” attached to a larger request or a compliment in a compliment and criticism sandwich, send them a note solely to share your appreciation for their work. Beyond just being a nice thing to do, you will help your colleagues understand their own strengths and what best practices to keep implementing. Moreover, if and when you have to share more critical feedback down the line, it will be received much better.

Get to know everyone. Meet as many people as possible. While you certainly interact with your closest collaborators regularly, you never know what future projects or situations may hold. It always helps to have allies and friends throughout the company. Use Slack’s Donut feature to have virtual coffees with other people. If you are on a group call with people you do not yet know, reach out to get to know them afterwards.

From output to outcome accountability

In VC, as an associate, my KPIs were largely centered around metrics like number of founders I was reaching out to, number of investors I was meeting with, or number of founders I was speaking to. These metrics were of course important and involved tons of hard work, but they were largely in my control to achieve and very output oriented. In contrast, in the operator world, as a growth marketer, my KPIs are largely outcome oriented, including things like marketing qualified leads, discovery calls scheduled, and revenue booked. While output certainly matters, the outcomes matter more. I could work harder than anyone but if the outcomes were not improving, my performance would be understandably deemed worse than if I worked less but achieved consistently strong outcomes. These outcomes are partly in my control but also rely on reactions and engagement from prospects. In this transition to being outcome, not output oriented, I have learned:

Value quality over quantity. A part of this mindset shift was disassociating time from output and finding ways to nonlinearly create output. It is human nature (and perhaps my nature especially!) to want to see results immediately, but I grew to understand that sometimes hours of research, discussion, and other work are needed to get to a single insight. While at first glance the ROI of this practice seems frustratingly low, I realized that it is this singular insight that can pay enormous, compounding dividends in all that comes after by raising the efficacy of everything from product development to campaign management to prospect calls.

Take time to reflect. Reflecting can often feel like an empty word or an actionless waste of time, but it is truly crucial to growth and improvement. At the end of each day, I asked myself pointed questions: what mistakes did I make? What surprised me? What did I learn? What do I want to investigate further? I then take running notes on these, pull out the key insights, and transform the learnings into actions (through adding them to meeting agendas, work products, or to do items on my calendar).

Prioritize thoughtfully. In marketing, there are so many channels, campaigns, and tactics that you can employ. Oftentimes, the greater challenge is not in merely executing on all of these but rather understanding the relative value and tradeoffs of each strategy as it relates to your product and target demographic specifically. There is a tendency to throw spaghetti at the wall until something magically sticks, but the greater ROI is achieved through thinking deeply about each option from a first principles perspective, experimenting at small scales, and thoughtfully moving from a broad selection of avenues to funneling the majority of resources into the projects that show the greatest promise.

See ideas all around you. Many people, myself included, spend hours each week scrolling through platforms like LinkedIn, shopping sites, and Instagram. Instead of just seeing this as inevitable wasted time, I brought a newfound curiosity to this seemingly mindless scrolling. On eCommerce websites, I noticed how companies structured their landing pages, tabs, and pop up windows to increase conversion. On Instagram, I noticed how companies leveraged multimedia content to build their brands. On LinkedIn, I noticed the copy and graphics that companies created to produce compelling banner ads. Each time I noticed something worthwhile, I wrote it down in a running ideas doc I kept and shared with my team.

Build repeatable processes. When you find success with a particular project or insight, think about how you can operationalize it. While the impact you create through this specific success is meaningful, the compounding effect of iterating and executing on it regularly over time drives exponentially more and better outcomes.

Think one step ahead. Instead of merely executing on projects per their tagline instructions, I envision the responses and reactions of those who will eventually utilize the work I am doing. For example, as I am writing copy for sales pitch decks, I put myself in the shoes of both the sales team and the prospects to identify the confusions they would have. I then adjust the pitch deck to anticipate these questions and address them through visuals or better messaging.

Operate at the lowest level of detail. When I was speaking with and writing about founders in VC, I used to think I was getting to the atomic unit of advice. But after starting as an operator in charge of implementing the strategies that founders had told me about in depth, I realized how wrong I was. People always say implementation is the majority of the work and is a significant determinant of success, but I never realized just how much (now I think it is practically 99% of the work involved!). Attention to detail is so incredibly important as an operator in everything from writing copy to prospect targeting to the exact word choice of sales call scripts to the products you choose to sell on your platform to the precise structure of your website to the number of calls to action you have on a page or in an email. Whenever I embark on a new project, I push myself to continuously flip these considerations into “how” questions to ask myself until I have clearly thought through every aspect of the final product.

Moving to the Other Side of the Table

In VC, I was in a unique giving part of the ecosystem. I was giving capital, time, advice, or introductions, which was wonderful and certainly hard work as well but a very different type of challenge from trying to sell a product to someone. On the operator side, you need to continuously demonstrate value to your prospects and customers. Your value does not simply come from your position in the ecosystem but is something you must earn daily. In my transition to this sales oriented role, I have learned:

Ask questions first. The #1 sales faux pas is to start talking about yourself and your product at the outset. People do not want to hear about any old solution. Rather, they want to learn about how you can help them and how your solution solves their specific problems. You cannot convey that without getting to know the prospect first. It is easy to read off a script and sell people a defined solution based on your agenda, but it is much harder yet so much more effective to convey a customized offering that perfectly meets the other party’s needs based on your deep research and understanding of them.

Listen to how people say things. Naturally, prospects will not be an open book to sales people, especially not on the very first call. While what they do share can be quite valuable, oftentimes what they do not share is equally, if not more valuable. When a prospect describes a challenge they faced, listen to the emotion behind their words: their tone and their pauses. Is this pain point part of a broader insecurity they have that they would love to address? Did this pain point manifest itself in a mistake that they were embarrassed by? Is this pain point a key bottleneck to the company’s success or their own success? By listening actively, you are able to more empathetically connect with the prospect and present a solution that addresses their most painful challenges.

Focus on the feeling, not the feature. People’s eyes glaze over when you get into the weeds of a multifaceted product, especially on the first call. While your own solution makes all the sense to you, it is much more foreign, not to mention less pertinent for your prospect. Instead of discussing every feature of your product, focus on the feeling behind the challenges you solve and the impact you create. What instincts do your prospects have? Are they incredibly organized? Are they risk takers? Are they deeply analytical? Demonstrate how your product speaks to their specific instincts. Convey a feeling of control for the incredibly organized prospect. Quantify the unknowns for the analytical people. Convey a daring, invincible feeling to the risk taking prospect.

Get to the atomic unit of insight. When speaking with prospects or reflecting on sales call recordings, move beyond the specifics of what the prospect is saying and look for the broadly applicable insight that is likely shared among people in your target audience. Sure the particulars of every prospect’s situation are good to know, but ask yourself what is it they are really saying? For example, if a prospect talks extensively about a time when their existing solution’s customer service was not there for them, you may infer that high touch service is crucial to them and a key value driver for your target demographic.

Give first. Create tons of value for people and ask nothing in return. In doing so, you establish trust and a genuine bond. Too often content marketing and other growth initiatives are purely relaying the benefits of the solution being sold. Instead, play the long game: create content that tactically supports your target audience without an immediate ask. Put on events and develop other resources that help your target audience grow their network, meet their own prospects, and learn. By giving first, your target audience gradually associates your name with credibility and are more likely to become your long term partner.

Finding Fulfillment

Every time I had to say no to incredible founders in VC, I felt some level of heartbreak. When I left VC, I was worried I would inevitably be separated from the ecosystem of founders I had loved being a part of. However, to my pleasant surprise, I have been able to stay connected in a perhaps even better and more meaningful way. Instead of having to constantly say no to funding amazing people, I am able to coach founders on fundraising and go to market in newfound ways. I began angel investing and while much of what I learned in VC about evaluating companies has been quite applicable, I feel the connection I have through my personal investments in companies to be that much stronger.

While I loved my time in VC and the team and founders I worked with there, I did often feel that the sheer breadth of the fund’s focus (covering every sector and geography) made it a bit challenging to find mission alignment. Of course, this is not true for everyone. Many people find that this diversity of focus is exactly what they look for and is what creates meaning for them in their role. However, for me, through contrasting my time as an operator and in VC, I realized that having an industry and product focus has motivated me more than ever before.

While I was very self directed in VC, I now find myself actually thinking about growth initiatives before bed or waking up in the middle of the night to write down ideas I had for articles or campaigns. Instead of listening to music or even podcasts, I find myself opening Gong to listen to our sales recordings. Even on holidays, I found myself, entirely of my own accord, writing new content pieces for our blog. On the weekends, I look for potential partners.

As I noted in my article of reflections after leaving VC, your career is less a journey to a preset pinnacle and more a constant process of finding your own product market fit. Even beyond the skills I learned as an operator, I am so grateful to have learned more about myself.

Chief of Staff at Beacons | Harvard alum | https://beacons.ai/jessicali