This version of the video doesn’t have the automatic transcription of the original podcast. I have created a better transcription below. I encourage you to read it here.

Brian’s podcast was titled The Top 3 Things You Need To Do To Close Large Enterprise Deals. We summarize those three things in the final moments of our conversation:

1. Practice at being a well-rounded person. 
2. Practice at being a business person. 
3. Be able to relate to your customer in a way that makes them successful.

I would also add a 4th attribute that we discuss in the podcast, but Brian doesn’t emphasize in this podcast (but he does in his other episodes):

ABL – Always Be Learning

I hope you enjoy the podcast. The transcript is below the video.

Brian G. Burns  

Sean, welcome to the show. As a way of getting started, tell us about yourself.

Sean O’Shaughnessey  

Thanks, Brian, I enjoy being here. I am Sean O’Shaughnessey. I’m currently the Chief Revenue Officer for Agile Stacks, a startup company based in California. I’m in the Midwest, though, because I cover the entire world. I can be anywhere.

I have a long history of selling enterprise IT solutions. I have worked for many large companies that are names everybody’s heard of on your program.

Brian G. Burns  

It was kind of weird that before I looked at your profile, I was expecting an Irish accent.

Sean O’Shaughnessey  

A lot of people say that, but I’m a seventh-generation Irish. I have a lot of German blood in me as well. But I’m the seventh generation. The first generation O’Shaughnessey that came over on the boat was back in about 1820 or 1830. Something like that. So we have been in America for a long time. I didn’t look like an Irish man. I’ve got gray hair, of course, but blonde hair originally.

Brian G. Burns  

You can pass as an Irishman. But yeah, you spell your name the same way my brother does. And yes, so he grew up with everyone calling him “seen.” Yeah. Have you experienced that?

Sean O’Shaughnessey  

Absolutely. Thank goodness for Sean Connery. I think I’m actually named after Sean Connery. I think my mother, God rest her soul, had a crush on Sean Connery. 

Brian G. Burns  

How did you get into sales? 

Sean O’Shaughnessey  

My father was a salesperson. My brother was a salesperson. I was originally trained as a mechanical engineer. I realized that I didn’t want to be a mechanical engineer. My last day of being a mechanical engineer is when I walked across the stage to get that diploma. I immediately went into sales.

I went to a really great program put out by Allen-Bradley, which was a whole year of sales training. It was almost like getting a Master’s in Sales. And I never looked back. I never wanted to be a mechanical engineer. I was more on the business side. I’m technically adept, but I just enjoy selling. I enjoyed being with people. I definitely don’t like being stuck in the office, like I am now with this stupid COVID thing where I can’t go to see customers. 

Brian G. Burns  

You miss the traveling? 

Sean O’Shaughnessey  

I do. When you’re traveling, you hate it. When you don’t travel, after doing this so long, it just feels wrong. I think my suitcase is dusty.

Brian G. Burns  

That’s it. You get used to looking at bad TVs and bad hotel food and not waking up not knowing where you are.

Sean O’Shaughnessey  

Exactly. I think the biggest thing is my wife is saying, “Get out of the house!”

There is more to read. Go to the following pages to read:
Introduction
Why does Sean like the sales profession?
The transition from salesperson to sales manager
Growth milestones
Rep radar and Always Be Learning

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.

This post originally appeared on my blog series on my company website “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup.”