Going From Enterprise Sales Manager To Startup VP of Sales? Velocity And Focus Are Your New Normal

Posted by Sean O'Shaughnessey on Oct 6, 2019 1:01:00 AM
Sean O'Shaughnessey
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The next in our series “Skinned knees—what an MBA didn't teach you for rebel sales in a software startup” where we discuss your promotion from individual contributor to leading a team. Is it for the faint of heart?

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Navigating the move from enterprise executive to startup VP of Sales or Chief Revenue Officer is not for the faint of heart. However, for successful managers, the disruptive nature of startups can be cathartic.

You are probably a lot like me. You went from an individual contributor or a front-line sales manager for a big company with lots of resources to a team lead at a small company with limited resources. A sales manager at a major corporation and an executive at a startup may seem like they have more differences than similarities, but experience in the former helps inform the latter.

For executives considering doing this move (or if you have already made the jump), this move is wide open with opportunity. Here's how to take advantage of it.

Know Your 'Why'

The grass is not always greener. Startups are not a reprieve from corporate life; they live on the razor’s edge of "scale or die." Time and mediocrity are enemies. Startups typically move fast to create solutions that can scale across industries and sectors.

In this environment, it's important to have a "why." The "why" is different for every executive -- and truthfully, it can be quite personal. Some questions executives may want to ask themselves while considering the move include:

  • Do I want to build solutions to problems I've encountered throughout my career?
  • Do I want to get back to creating?

For example, our customers get the benefit of Kubernetes. According to Gartner, containers and using Kubernetes to orchestrate containers is the de facto choice for the next generation of software infrastructure. When I saw the reference architecture for Agile Stacks, I knew we had a game-changer that enterprise buyers need because every company on the digital transformation journey must build software better and faster. And the velocity, matched with a rigorous focus, is what I need at this stage of my career.

Find Your 'Who'

I was introduced to my current startup by one of their Board members that I have known for years. When I met the CEO, I found that we shared similar industry observations, and I found myself excited about his market vision, company, and approach.

If you are joining an existing founder, you have a lot of research that you must do and it won’t be as easy as joining a big company with a lot of documentation. Research the company beyond financials, business model, product, and technology. Understand the startup’s culture; invest time and effort into exploring whether the executive-partner relationship can build a foundation for mutual success.

Assess Your Industry Expertise

Soon after talking to the company, I realized my new company had built actual solutions for some of the problems I had on the enterprise side. I could leverage my industry expertise to help the company execute its product vision, accelerate time to market and deliver quality solutions. When I considered leaving a global enterprise for a startup, it had to be the right one.

Startups should meet or beat milestones, and the industry expertise of their leaders can be a driving force to provide rigor. Executives must self-assess how deep and how broad their industry knowledge is. Do you fully understand the ecosystem and how you can help a startup impact, and potentially lead, that industry? Can you bring market vision, build strategic partnerships, drive maturation in existing products, expand the book of business, develop talent, deepen customer relationships, or create operational efficiencies to enable faster growth?

Fight Through Ambiguity

There is no room in a startup for executives who are unwilling or unable to be operational and visionary. It is not possible to understate the level of foresight, flexibility, and agility required in this environment.

You must continuously recalibrate your approach to operational efficiency, as working with limited resources forces me to ensure I am creating value at every turn.

Create Value

Within many large companies, the Silicon Valley mantra of “move fast and break things” doesn’t necessarily translate. Large companies have the resources, money and institutional support unavailable to start-ups, but they rarely have the focus to solve industry-sized problems. And they must measure and manage risk daily.

Further, while startups are relatively flat, large corporations are highly matrixed. In order to be a successful sales executive, it’s imperative to build relationships across departments. People need to trust that moving forward will benefit them.

Any executive joining a startup should focus on the value they create as an individual. What do you bring, above and beyond the job for which you were hired? Ask yourself if you have the emotional quotient (EQ), for example, to serve as a translator to the enterprise on how to evaluate product fit while coaching a startup team on how best to work within enterprise processes for implementation. That's creating value for both sides.

Get Accustomed To The New Normal

Velocity and focus are my new normal. You must create more with less, fast and with laser-focus on impact. Startups can accomplish more in weeks than a large company could do in years, if at all. However, that rapid advancement can easily cause the company to go into disarray. It is simply not enough to have velocity, you need to have velocity towards your goals as a company.

Topics: Startup, Sales, Business Development

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