Head of Sales

GROWTH NAVIGATOR (Head of Sales)

LOCATION: 100% Remote with regular visits to HQ

ABOUT RAISE AWAY: we provide kick-ass fundraising solutions to nonprofits and schools, specializing in luxury travel.

OUR CORE VALUES: Fun, Unique, Creative

ABOUT THE ROLE

Growth Navigator (Head of Sales)

Real talk: the easy close stopped doing anything for you a while ago. You could sell ice to an eskimo, but who cares? You've done that. What actually gets you going is the build. The system. The playbook. A team that closes clean whether or not you're on the call.

But building that kind of machine takes more than just wanting it. You've got to know what's under the hood. CAC, LTV, conversion velocity, GTM. You didn't have to look any of those up, and don’t lie, you definitely judge people a little when they do. They're just the language you think in. It's the same instinct that has you quietly winning at Catan while everyone else is still arguing over who gets the wheat. Strategy isn't a switch you flip. It's how you read the room, the board, and the pipeline, all of it.

Here's what matters. We're not looking for a manager who forgot how to sell, or a closer who can't grow a team. We want both, all wrapped up in one. A real player-coach. Someone who'll happily jump on a call for a big account, then turn around and build the thing that makes the next ten reps great. You'll draw the map and walk it. That's the gig.

And this one's got room to grow. You'll start hands-on, prove the sales cycle actually works, then earn the space to build something bigger. Where it's headed: Director of Sales (new fun title loading…) in 3 years, with a sales manager and a key accounts manager reporting to you. We're not just waving that around to look shiny. If you're the right person, the runway is real.

A DAY IN THE LIFE OF A GROWTH NAVIGATOR

40% In the Game (Management)

• Coach and grow the Account Executive team
• Build sales pipelines, lead workflows, and lead-management strategy
• Close deals and ride along with reps on key accounts
• Review the tapes. Sit in on calls and recordings, then coach what you hear
• Keep an eye on daily and weekly activity so reps hit their targets

40% Charting the Map (Strategy)

• Dig into conversion rates, deal size, and velocity
• Report and forecast with numbers you'd bet your own paycheck on
• Run strategy across marketing, finance, and product
• Live in CAC and LTV. Know exactly what a customer costs and what they're worth
• Build the playbook for new territories and markets, and keep it fresh
• Lead the planning as we crack open new markets nobody's touched yet

20% Behind the Curtain (Operational)

• Hire, recruit, and train the people who become your A-team
• Reports directly to the CEO
• Get every bit of value you can out of Hubspot

THE MULTI-YEAR PLAN

First 6 months, you're 80% manager. Get in the weeds, prove every piece of the sales cycle works, and call out the stuff that doesn't. The next 12 months, half your time shifts to director work. Planning, building, becoming the architect of sales. Two to three years out, the goal is you sitting in the Director of Sales seat with a team reporting up to you. Big role. We mean it.

RESPONSIBILITIES

• Own monthly and quarterly goals, yours and the team's
• Build the sales budget for this year and next
• Coach, grow, and keep A-players around
• Close deals and team up with reps on key accounts
• Build and maintain pipeline, lead workflows, and the sales playbook
• Make sense of the numbers that matter and forecast with confidence
• Drive expansion into new territories and markets
• Work hand in hand with marketing, finance, and product
• Hire and build out the sales team
• Get the most out of Hubspot and report to the CEO
• Ride a unicorn 🦄

Proof of Work

• 7+ years of total sales experience
• 3+ years of sales leadership experience
• A "scale-up" background. You've helped something grow, not just kept the lights on

Technical & Strategy Skills

• GTM knowledge you've actually lived, not just read about
• Comfortable with the data. CAC, LTV, and conversion rates are second nature
• CRM mastery (Hubspot is a plus)

The DNA

• Full-cycle selling. You can still run the whole thing yourself
• A coaching instinct. You know how to build A-players and keep them
• Communication that works in a boardroom and on a cold call

WHAT YOU GET

• A role at a Kick-Ass company
• Unlimited vacation, Bali here you come!
• Flexible work environment, 100% remote
• Paycheck…the obvious one
• $120,000-$140,000 starting salary (final number dependent on experience)
• Travel to some amazing destinations around the world - we just got back from a company African Safari trip!
• Benefits, yay! (Health & Dental & 401K & Life Insurance)
• Passport Program. Get a Raise Away trip 1x a year on us, plus airfare!
• Level Up. An internal fund to help you grow personally and professionally

NEXT STEPS

Here's what the hiring process looks like, assuming things go well with your candidacy.

1. Application
2. 20-minute pre-interview
3. 30-minute interview with hiring manager
4. 30-minute interview with Raise Away team member
5. 45-minute interview with CEO
6. Final assignments & assessments
7. Offer!
   

TO GET THE PROCESS STARTED, SEND US:

• Resume
• Cover letter showing your personality. Seriously. No boring corporate bull shit allowed
• A drawing of a paper airplane flying through the universe (not joking)