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The Hired Gun Approach

For those not familiar with my story, I was Chief Revenue Officer (eventually GM) of Internet Performance company, Dyn, on our path to $100M ARR and a successful exit to Oracle in late 2016. Many people assume I was a founder because of how early I joined the business, my value delivered, and my leadership role and tenure… but the truth is, I was a hired gun in 2008 which was seven years after the founding of the initial consumer focused ecommerce business. I was brought on to build an enterprise brand, build a growth machine, and focus on B2B sales.

Dyn was relatively successful before I arrived, but all great technology companies either grow or die. Gosh, I say that a lot. Co-Founders Jeremy Hitchcock and Tom Daly, the CEO and CTO respectively at the time, knew that innately. But the change that was coming was hard to predict. It’s critical for founders to self-reflect, know their strengths and weaknesses, understand their experiences, priorities and interests and build great teams around them. In many instances, they need to bring on a hired gun or many hired guns to bring their company to the next level.

hired gun

Noun informal • North American

noun: hired gun; plural noun: hired guns

  1. a hired bodyguard, mercenary, or assassin.
  2. an expert brought in to resolve complex problems or to lobby for a cause.

All companies need their leadership teams to be made up of complementary parts, but it’s especially true in startups. Sustained success comes with growth from cross-functional, diverse and fully-formed teams working towards an aligned vision. Often, like in my case and numerous other startups, these hires become the growth catalyst the company needed to scale.

I’ve written in the past about personal development and career evolution in a growth startup, as it’s not for the faint of heart. But landing the job, fitting in upfront, and establishing trust can be some of the hardest days for a hired gun. It can be a lonely island.

I was recently asked what advice I would give someone coming into an early-stage startup in the hired gun role, specifically in the go-to-market leadership position to run marketing, sales and customers. Getting the founders to hand the keys to the outside game business building is not easy for them, but when they do and can, the sky becomes the limit.

The hired gun approach needs to be pretty simple:

  • Be tactful
  • Be strategic
  • Be patient
  • Be more than a sales guy or gal
  • Be a learner
  • Be collaborative
  • … Pick your spots!

Don’t be a bull in a china shop and hit the streets before you, or more importantly, the company is ready. Understand the market, segments, verticals, personas, value prop and use cases. Learn the technology by cozying up and being best friends with the technology and product leaders on this ride with you. Play the game. Play the long game. Find out what other colleagues are playing for. What motivates the team? What excites them? What part do they play in the company machine? Find your tech/product counterparts and make best friends with them (wait, I already said that). You need them to be successful. You need everyone to be successful so care and build meaningful relationships.

The first thing I recommend and what I did was hone in on “the pitch” — the narrative that the company story would be built upon that weaves all players into it. We package this up now at York IE into a business strategy and messaging hierarchy exercise with our portfolio and advisory clients. It then gets cascaded into decks, websites, sales collateral, everywhere, what I like to call “the bag of tricks” that includes all resources required to build a go-to-market (GTM) engine. Only then, can you implement drumbeat marketing to build a brand.

Back then, like now, it is important that all employees buy into this public-facing vision and evangelize it until blue in the face. For a hired gun to be successful, they must embrace company culture, get along with people, and rally people together as the chief evangelist inside the walls almost as equally as outside them. It was imperative back in 2008 that the company believed in me and had my back. It’s even more so today in this remote and digital economy.

Startup GTM leader 101: know what you need to know, know what you don’t, draw the line, plug holes, use the resources around you, win deals, win more! Become the hired gun you aspire to be and that future hired guns will want to emulate!

Sales Team Structure Template

Set your sales org up for success with the templates and frameworks in our free GTM strategy playbook.

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Sales Team Structure Template

Set your sales org up for success with the templates and frameworks in our free GTM strategy playbook.

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