The 3 Stages of Hiring GTM Executives

I hope you’re starting off the week strong.

The GTMfund team has been spread across the globe lately, big things happening!

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Dreamforce in SF last week for our GP, Max Altschuler.

Singapore for our newest Partner, Paul Irving (well deserved and overdue!).

And NYC for myself.

The rest of the team is playing catch-up from SaaStr followed by our annual GTMfund retreat in Napa. It was truly a special weekend with an incredible community of GTM leaders and operators.

Filled with gratitude coming out of it.

Anyway, let’s get into it.

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Last week we did Part 1 on SaaStr takeaways w. David Sacks – GP at Craft Ventures, and this week I thought I’d wrap it up with Part 2 stemming from a great session with Spenser Skates, CEO and CoFounder of Amplitude.

He brought up a very interesting topic that many GTM leaders / founders face as a challenge when scaling a startup; highlighting the 3 stages of executive hires as you scale and what to look out for qualitatively

Spenser Skates highlighted 3 main points on what it means to build a long- lasting sustainable business:

  1. Maintain a culture of product innovation: Product is always getting better as you use it, but it’s hard to do as you scale. 

Why? Because Innovation inevitably (but not exclusively) goes down as you scale. 

Solution: Build functional teams that drive innovation.

You can do this through

  • Weekly product demo’s on weekly company wide meetings

  • Create feature release slack channels 

Execute week-long internal “Hackathons”

  1. Treat new products like a mini startup

As you get to 100M in ARR you want to find new pieces of value outside of your core offering (this is hard) How can you then achieve this?

  • Coordinate with other teams in the org (go-to-market, compliance teams) to help the central product team be successful

  • Get something out there that has paying customers right off the bat (always have a value driven mindset)

  • Bring in people who already know the new problem space that you’re solving for. Often they have been building something in an adjacent category. Why does this help? You don’t need to get them up to speed in the space and you’ll benefit from their tribal knowledge that may not already exist internally. These people will significantly help accelerate each new product launch.

  1. The 3 stages of executive hires

This pillar is what we’ll focus on for the bulk of this newsletter and we brought along some of our friends to weigh in:

The 3 stages of executive hires

Early Stage ($1-$25M)

You need an executive who’s strong at operating in a non-structured environment and can create something out of nothing (0-1). You need to hire people who are very much think like you, as a founder.

Let’s see what some of our best GTM operators have to say as experienced founders / executives who have experienced hiring early stage:

Manny Ataebi 6x Marketing Leader & Advisor

Going to speak from the POV of being the person in bullets one and two. First bullet is definitely creative grinders. People who think out of the box and don’t get rattled by change. Doers with a ton of hunger and drive. Second bullet is the same but also can hire folks around them and in that same level of effort in enablement and recruiting so they can get those same players and more importantly enable them to succeed and keep them in the company.

Paul Mander GTM Executive & Advisor

This person should be someone who has done it before and wants to do it again, or someone who is on the cusp of being an exec and wants to/can do the building to position themselves as the leader that the team can be built around. They have to be able to set the vision and then also be a doer themselves initially and then alongside their team.

David Teichner Co-Founder at Accelerate

At the early stage, can the person succeed in chaos/lack of structure? Going from 0-1 takes a certain mindset. The person needs to be willing to wear multiple hats, work hard, iterate, fail fast, pivot, etc. None of this intimidates them…they thrive in it.

Justin Stackany CEO / Startup Advisor & Former CCO

Hungry generalists who are uncomfortable being bored and secretly enjoy a little chaos. They probably did poorly in school (despite their high test scores), but instead got really into arcane subjects like Russian History (lol).

Mid Stage ($25-100M)

So as you get to the 10’s of millions in ARR, you need to transition your hiring profile.

You change from hiring someone who’s scrappy, to hiring someone who’s able to take something that’s already happening, repeat it and build systems/processes. 

Note: a lot of people who were really good early on, aren’t good at this stage.

A few more thoughts we gathered from experienced GTM founders / operators:

Paul Mander GTM Executive & Advisor

This hire understands what it means to scale – they can see where processes are nonexistent, brittle or inefficient, and can fix it…they can spot single points of failure and build process around it. They get that what worked before may not work anymore.

…At all stages – they must be intellectually curious and never be the person that says “this is how its done and I know it so that’s why we’re doing it”.

David Teichner Co-Founder at Accelerate

At mid stage, can this person take lessons they learned…develop repeatable processes for scale?  As the company is maturing, there are more leaders and departments so this person will need to have the ability to work cross departmentally and be flexible/welcoming to feedback.

Justin Stackany CEO / Startup Advisor & Former CCO

Now you’re starting to actually build out some real departments. You need to look for HPELs (high-potential entry-level). You should be investing in onboarding programs and finally deal with your shitty bloated CRM and build out a single source of truth.  Executive team that can scale globally and through an acquisition is important, so things get more complex. Many of your early-stage leadership can’t hang here, so you’ll need to figure out what to do with them.

Late Stage ($100M+)

At this stage, you are no longer hiring executives who do the work themselves; you’re hiring people who are good at delegating. Their superpower is based on hiring other leaders.

Once you get to 100+ in ARR, there are so many different variations of complexities within the org. and need role players that won’t go rogue.

Final thoughts from experienced GTM leaders at this stage:

David Teichner Co-Founder at Accelerate

At late stage, bureaucracy kicks in. People have to be good at advocating and communicating business strategy with clear business cases/justification. There’s a lot of managing up/managing sideways/managing down, etc., more so than at the earlier stages.

Justin Stackany CEO / Startup Advisor & Former CCO

It starts to take a long time to get things done here. Departmental silos and knowledge gaps start to materialize. You need leaders who can really architect, stay on brand, and understand that exec team is first team. Diversity and inclusion are a priority if you haven’t addressed early.

Something worth highlighting as we wrap up, is the emotional element that comes with hiring and firing as you scale up.

It’s difficult to move on from people who helped build your company, but you need to find ways to detach from the emotional element and focus on the best business decision (it won’t be easy).

You can do unscalable things to a certain point, then the paradigm shifts on you and you have to learn to say “no” and “goodbye” a lot more.

👀 More for your eyeballs

👂 More for your eardrums:

Throwback to our first GTM episode with the infamous, Mark Cranney. This is still one of the most listened to episodes that we’ve recorded.

🚀 Start-ups to watch: 

Keep an 👀 on the team at Wynter!

🔥Hottest GTM job of the week:

Marketing Lead at Wynter, more details here.

See more top GTM jobs here

That’s it, that’s all.

Appreciate the continued support, it was great to meet many of our readers in SF and NYC over the last few weeks – always appreciate the love.

Have a great week ahead.

Barker ✌️

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Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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