Sales Onboarding & Enablement Lead

Hi! I’m Matthias, and I’m leading Sales at Modash.

I’m looking for a Sales Onboarding & Enablement Lead for the first time.

Below is the context for why we’re hiring, what you’ll own, and things you probably want to know.

Our sales team is ~10 people across the Toronto area and Europe. We want to double output over the next 18 months, which means ramping the current team and hiring a lot more people. Two big gaps led us here:

• Onboarding - We need to take our current process & build it into a system that’s able to turn all newly hired Account Executives into high-performing champions in a short amount of time.
• Enablement - We don't currently have anyone owning the creation, quality, and accuracy of the internal resources and training materials that help our entire sales team deliver consistently the best possible customer experiences.

We’ve reached the high growth stage where the only way for us to succeed is to have a dedicated person spending 100% of their time perfecting these systems.

I believe onboarding/enablement goes hand in hand & can be handled together by the right person!

The background above covers the broad scope pretty well, but here I'll elaborate a little more on what these initial projects might look like for you.

You'll create an onboarding program that gets new AEs up to speed fast.

That includes:

• Defining structure, curriculum, pacing, and setting weekly expectations
• Creating onboarding materials (docs, call library, exercises, quizzes, role-plays - we trust you to figure out what works best)
• Running the day-to-day: 1:1s, call reviews, shadowing, role-playing, and feedback loops

You'll figure out what "on track" actually looks like for a new AE and build a simple system to track it week by week, so nobody's guessing whether things are going well.

What you'll actually be tracking:

• Call quality (are they running good calls? asking the right questions? setting solid next steps?)
• CRM hygiene (are deals tagged, valued, and documented properly?)
• Growth habits (are they prepping for 1:1s? asking for help when stuck? thinking ahead on deals?)

The point is simple: every new AE should know exactly where they stand, and so should we. No guessing.

You'll own all of our sales enablement resources:

• Identify gaps and create resources (playbooks, objection handling, best practices, explainers, battle cards)
• Keep everything up to date as our processes and experiments change
• Make sure our AI tools always pull from the latest stuff
• Actually get the team to use it (not just build it and hope for the best)

You'll report to me (Matthias) and work closely with marketing and success on enablement projects.

A few more things that may be useful to know about the team:

• Our AEs are split across North America & Europe. 70% of the AEs are in NA. For this reason, we are looking to hire you to Toronto area, Canada as well.
• We are fully inbound driven - Marketing is responsible for delivering 100% of our call-bookings. This means our AEs spend all their time on calls and giving customers the best experience possible.
• Today we primarily focus on selling influencer marketing software to consumer brands (i.e Stanley 1913, Victoria’s Secret, NordVPN etc…)
• Sales cycles can be anything from 0 to 6 weeks or 2 to 6 months based on the complexity & size of the deal. (I.e closing a small Shopify Store vs closing large enterprise deals)
• We have Steven on the team fully dedicated to Sales Operations who can help with anything technical or data related
• The team uses Hubspot, Notion & Avoma to manage deals, plus some custom internal tools.

You should be:

• Experienced building and leading a sales onboarding and/or enablement program from the ground up (not just inheriting one)
• Experienced in B2B SaaS with consultative sales
• Great at absorbing information and writing - you can take something complex and turn it into something clear that anyone on the team can use
• Someone who can coach and give honest, direct feedback - not sugarcoated, but constructive
• Self-sufficient - you solve problems, make decisions, ship, measure, iterate. You don't need to be managed
• Good at researching problems, coming up with solutions, and actually executing on them

• You've been in a sales org that successfully went through rapid growth before
• Startup experience
• You've worked in an inbound-driven, customer-first sales environment
• You care about influencer marketing & the creator economy

• Flexible hours ⏱ You'll ideally start your day early in the morning to work to work with colleagues based in Europe. Most of the sales organisation is based in Toronto area, Canada together with you. But, nobody will be looking over your shoulder. Start late, finish early, run errands during the day. Whatever you need, as long as the work gets done. We are all adults here.
• Unlimited paid vacation 🌴 If you're rested and happy, you do better work. Take what you need.
• Remote-friendly 🏠 Your home base needs to be the Toronto area - beyond that, work wherever you do your best work. Home, café, beach, co-working space. As long as you've got reliable internet, we don't mind.
• Compensation 💸 of 130-160k CAD annual + stock options is what we have planned, but we are open to discussing this further.
• Personal development budget 🧠 Courses, books, conferences. If it makes you better at your job, we'll cover it.
• Real ownership 💡 You're the expert. Make decisions, move fast. No unnecessary red tape.