What I Learned After Spending Two Years in Venture Capital

OpenView has always been unique in the VC space because of their support model. Ten years ago, Scott Maxwell founded the firm with a singular focus in mind – invest in and help grow expansion stage software companies. This allows OpenView to dive into their portfolio and make a huge impact.

It’s also the perfect place to learn.

When I first heard about the Head of Marketing role at OpenView I believed it was the perfect opportunity for me. I had accomplished what I was hired to do at ExactTarget (and ultimately Salesforce) by building and scaling a successful content team. We were humming and producing content all over the world. This new opportunity was the perfect way to gain in-depth knowledge on how to build and scale software companies and it was.

My role was designed to build the brand, position OpenView as a thought leader for expansion stage software companies, and build a stronger foundation for the future. The team has accomplished this mission many times over through a dramatic increase in our content quality, our rebrand, and an overhaul of messaging. We now have a system in place for the firm to accomplish even more and it made me realize my job here is done. It’s time to jump back into an operator role and find a company to build from the ground up.

The lessons I learned watching the partners, my colleagues, portfolio CEOs, countless pitch meetings and hundreds of conversations between leadership teams was invaluable.

Here are a few.

Experiences First. Tactics Second.

Many marketers (and CEOs) get this wrong. They have the tendency to think of channels and tactics first and the experiences second when planning a marketing strategy. It’s the wrong way. Start with the experiences and follow with tactics and KPIs. It will help focus your time and energy as a company.

  1. Pick your most important target persona first. At OpenView our primary target persona was a CEO of an early-stage software company.
  2. Build your target persona journey stages. We focused on four stages: Awareness, Interest, Consideration and Commitment. A software company may look a little different: Awareness, Consideration, Purchase, Usage and Advocacy.
  3. List all experiences within each stage of the persona journey. Meet with every stakeholder in the company to get an exhaustive list. This should come from sales, product, customer success, marketing, and finance. Everyone. Example from OpenView: The CEO gains social proof by being referred to OpenView’s content or website by someone they trust. Win/loss reviews are also a great way to define the right experiences.
  4. Pick the top 3-4 experiences for each stage. Talk to your top customers and influencers to help define the best experiences. Don’t accept your internal team’s opinion as truth.
  5. Apply tactics to each of the experiences. OpenView example: If we wanted the prospect CEO to “gain social proof from someone they trust” our tactic would be Influencer Marketing.
  6. Apply KPIs to each of the tactics. OpenView example: If influencer marketing is our tactic our KPIs would be the following: X times feature on influencer blog, x times featured in top SaaS resource, x times shared by influencer on Twitter, etc.
  7. Build project plans around the KPIs and tactics. If we wanted to be featured on influencer blogs we need to start by building a list around top blogs to target and go from there. Each KPI should have a project plan to reach it.

Here’s an example of the planning doc:

It’s a reverse planning process but works extremely well when focusing the entire organization on the top tactics and experiences associated with the top target personas.

Focus & Alignment Drive Growth

Speaking of focus… when you are growing a software company (moving from startup/see to expansion) nothing is more important. Hunting and killing is everything as you try to find product market fit but once you scale focus should take priority. Focus on data to make informed decision when picking the right targets and verticals.

Dennis Mortensen, x.ai’s Founder and CEO said it best from an interview we completed in 2015 on why he runs his company on one KPI:

“The idea of a startup is just so fragile that the default outcome is almost always that you don’t make it. To ensure success, you need to make sure that everybody is running in the same direction. And the more aligned you are, the more likely it is that you will have a good outcome.”

All companies break at certain points as they scale. It is inevitable. The most common issues fall within alignment between teams. This is especially true for marketing and sales. Spend time at the very beginning gaining consensus from your marketing and sales leaders on the right measurements and plan for enablement.

Every Employee Should Demo

I’m a huge fan of Alex Rosemblat, VP of Marketing at Datadog. He is a brilliant tactician and is one of the best at marketing technical products. Here’s an excerpt from an interview we conducted earlier this year:

Rosemblat has always worked on highly technical products, and Datadog is no different. To sell effectively, he needs a team of marketers and salespeople who are fully versed in the lingo, the product use cases and the customer needs.

Unfortunately for Alex (and many marketers in the technical space) it’s impossible to find highly technical marketing and sales professionals. Rosemblat takes a different approach. Find great players who might not have a technical background and invest a ton of time and energy in training them during the onboarding process.

“After someone has been with the company for a few months, they are ready for Rosemblat’s comprehensive demo certification training. Compressed into several hours of intensive training, this course pairs new hires with support engineers and product marketers. The goal is to walk new employees through the standard demo in great detail so that they don’t just learn what to say, but also why each element is there to begin with.”

ExactTarget had a similar onboarding process but not as intense. All employees spent one week building an introductory email using the product. It made every employee a user but not an influencer because they couldn’t pitch the product.

It shouldn’t matter what type of software you sell. Every employee from finance to sales should be able to pitch and sell the product.

Hire Operations Before Brand

Culture and brand building are extremely important to the success of any software company. However, the CEO and leadership team should be the culture carriers and brand “planners” in any expansion stage software company. Many companies make the mistake of hiring brand centric teams before operations.

Culture is important but securing and planning data input processes as you scale makes your company relevant. You don’t want to grow to $15-$20M in ARR and the entire system break because marketing/sales ops were not involved from the very beginning.

Embrace Unit Economics 

I learned very quickly that marketers spend way too much time obsessing over surface-level metrics such as ‘engagement,’ when they actually need to spend more time in unit economics.

Unit economics are the direct revenues and costs associated with a particular business model expressed on a per unit basis.

Some frequently used (or underused) metrics:

  • MRR (Monthly recurring revenue)
  • CLV (customer lifetime value)
  • CAC (customer acquisition cost)
  • Churn rate

All employees should understand the unit economics important to the business. Honestly, you should understand them as intimately as the CEO. This is especially true of the leadership team. I’ve met too many marketing, sales, product and support leaders that couldn’t tell me the CLV or CAC for their business. It’s dangerous and leads to bad decision making.

This is only a small list of all the knowledge I gained over the past two years while working in venture capital. Want some additional knowledge bombs? Feel free to check out my top posts:

  1. Power Expansion: Reinventing OpenView’s Brand from the Inside Out
  2. 4 Content Types of Own Thought Leadership in Any Market
  3. An Alternative Approach to Growth: One Part of the Funnel at a Time
  4. 6 SaaS Marketing Trends Learned while Scaling from $47M to $400M

Unfortunately for OpenView, they are not getting rid of me for good. I’m staying on as an Executive Advisor to help build the best portfolio companies on the planet. Other than that… I’m going to spend the next couple of months having conversations and meeting people all over the country. Want to chat? Feel free to hit me up on LinkedIn or Twitter.


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