Sales Strategy & Enablement Lead

About the Company

Makeship empowers influencers, creators, and brands of all sizes to develop and launch limited-edition products that matter to their fans. Leveraging our design, manufacturing, and marketing expertise, we work with our partners to bring their products to life through our community-powered crowdfunding platform. Each product is given a window of 21 days to be funded by the community before we produce and ship to fans worldwide. We put our brand behind every product and guarantee quality and ethical sourcing.

We're profitable; we have a three-year revenue growth of over 200%, ranking us 97th in 2024 and 86th on The Globe and Mail’s Canada’s Top Growing Companies of 2025 list. In 2025 alone, our sales exceeded $65M CAD. We are proud to be Great Place to Work-Certified™ for 3 years in a row! Learn more about us at Makeship.com.

About the Role

We are looking for a Sales Strategy & Enablement Lead who can take what great selling looks like here, sharpen it, scale it, and keep evolving it as we grow. This is a role for someone who understands people deeply. You know how to build trust fast, uncover what actually matters, make a value proposition click, handle objections before they become roadblocks, and tell a story that people remember.

But you're not just a great seller.

You know how to turn instinct into something teachable.

You can listen to a call and immediately hear what landed, what didn't, and what should change. You can rewrite the deck, sharpen the talk track, rethink the follow-up, coach the AE, and then look at the data to see whether it worked.
You won't carry an individual quota. Your impact will show up in the performance of the entire Partnerships team.

Reporting to the VP, Revenue, you’ll own how we approach, pitch, nurture, win, grow, and win back Creator relationships. Your closest business partner will be our Sales Manager, who owns day-to-day team leadership and performance. You’ll also work closely with RevOps, Marketing, Data, and teams across Makeship.

This is not a role where you sit on the sidelines and hand people frameworks.

You’ll be in sales calls. You’ll talk to Creators. You’ll coach AEs. You’ll challenge assumptions. You’ll test ideas. You’ll throw out what isn’t working. And when something starts working really well, you’ll figure out how to make the whole team better at it.

Makeship already has six years of learning, strong growth, and a lot that works. Your job is to understand why it works, make it better, and evolve it as we launch new products, enter new Creator verticals, and keep raising the bar.

What We Are Looking For

We’re looking for a salesperson first.

Someone with exceptional EQ, strong instincts, competitive energy, and a genuine understanding of how language, trust, relationships, and timing influence a sale.

You may be a top-performing AE, a sales strategy or enablement lead, or the person other sellers naturally come to when they need help closing something difficult. You may have built playbooks, mentored teammates, or moved into sales leadership.

Your title matters less to us than the pattern.

You've sold. You've learned what works. You've developed your own judgment. And at some point, you realized you were just as excited about making the team better as you were about winning the deal yourself.

Creator economy experience is a major advantage. Selling to Creators is not traditional B2B sales. Relationships are built through Instagram, Discord, YouTube, calls, DMs, and communities as often as they are through formal meetings.
You need to be comfortable in that world; or, come from another fast-moving, relationship-led environment where you’ve learned how to sell without hiding behind a rigid corporate playbook.

We move quickly. We’re competitive. We’re curious. We challenge each other, laugh a lot, and care deeply about doing great work. You should be confident enough to work independently, humble enough to change your mind, and comfortable jumping from a strategic conversation straight into the weeds.

Your Key Responsibilities

Sales Storytelling & Methodology:

Own and continuously evolve how Makeship sells.

• Turn Makeship’s value proposition, results, capabilities, and differentiators into a clear, memorable sales story.
• Personally develop and improve sales decks, talk tracks, discovery frameworks, pitch approaches, objection handling, nurture messaging, follow-up strategies, and playbooks.
• Help AEs and AMs understand not just what to say, but why it works and how to adapt the story to the Creator in front of them.
• Build a methodology flexible enough for emerging Creators, established Creators, and different Creator verticals.
• Adapt our approach as Makeship launches new products, enters new Creator verticals, or tests new ways of working with Creators.

Coaching & Enablement:

Make the team better at selling.

• Work directly with AEs through live coaching, call reviews, workshops, pitch development, and ongoing feedback.
• Own our sales enablement program, including onboarding, recurring training, playbooks, workshops, and certification.
• Partner closely with the Sales Manager so the methodology becomes part of ongoing team coaching. Identify what our strongest sellers are doing differently and make those behaviours repeatable across the team.

Creator Growth & Relationship Strategy:

Help us sell beyond the first drop in the Creator's best interest.

• Build frameworks that help AMs move from “we need another launch” to thoughtful Creator growth planning.
• Help define how teams should think about timing, product progression, Creator milestones, fan moments, tentpoles, and larger programs.
• Develop the questions, planning tools, and storytelling that help AMs build strategic roadmaps with Creators.
• Create win-back approaches for Creators whose relationship with Makeship has lapsed.

Competitive Strategy:

Make sure our team knows why Makeship wins.

• Stay close to competitors, their positioning, their offers, and changes in the Creator merchandise space.
• Turn competitive insight into better discovery, positioning, talk tracks, objection handling, and sales plays.
• Teach AEs and AMs how to recognize competitive threats, uncover weaknesses, and position Makeship naturally and confidently.
• Help build a team that knows how to assess the landscape in real time rather than relying on a static battlecard.

Testing, Data & Continuous Improvement:

Keep learning what works.

• Stay close to frontline conversations and use them to form hypotheses about what could make us better.
• Use funnel and performance data to understand what’s improving, where momentum is breaking down, and what to test next.
• Track signals including win rate, conversion, sales-cycle length, speed to first launch, repeat launches, expansion, and other measures of sales effectiveness.
• Work with RevOps and Data to define the reporting and insights you need.
• Test changes in messaging, follow-up, sequencing, pitch structure, and methodology, then keep what works and change what doesn’t.

Revenue Operations & Marketing Partnership:

Know what great selling needs, then help the right teams build it.

• Partner with RevOps on the sequences, workflows, CRM support, alerts, and tools that reinforce the sales methodology.
• Be comfortable working in HubSpot and hands-on enough to build or test simpler solutions yourself when it makes sense.
• Bring forward new sales technology when you believe it can make the team more effective.
• Partner with Marketing so Creator-facing content reinforces the same story our team is telling in the field.
• Identify the content and assets the sales team needs — from proof points and case studies to videos and Creator education — and work with Marketing to bring them to life.
• Bring frontline Creator insights back into the business so our broader messaging keeps getting stronger.

What You Bring

• 7+ years of sales experience, including significant time in a quota-carrying role, with strong live selling instincts and a track record of building trust fast, uncovering motivation, and adapting quickly.
• Evidence that you've made other sellers better through mentoring, coaching, sales leadership, or enablement.
• The ability to turn a complex value proposition into a simple, memorable story, and to build the practical tools that help others tell it, such as talk tracks, pitch decks, discovery frameworks, objection handling, and follow-up strategies.
• Experience in a startup, scale-up, or emerging category where the playbook was still being written, and a natural instinct to turn ambiguity into something clearer and more useful.
• Strong competitive instincts and curiosity about why buyers choose one option over another.
• Comfort interpreting sales funnel data and working in CRM and sales technology (ideally HubSpot) to improve performance.
• A collaborative, low-ego approach and the confidence to challenge an idea when you see a better one.

Bonus

• Experience selling to Creators, influencers, talent, communities, or other non-traditional business owners.
• Experience in the Creator economy, gaming, merchandise, crowdfunding, fandom-led commerce, or another community-driven industry.
• Experience adapting your sales approach across audience segments and verticals, from informal, relationship-led conversations to larger strategic accounts.
• Previous experience as a sales leader, or building and evolving a sales enablement program in a high-growth startup.
• Confidence speaking to groups, facilitating workshops, or representing a company externally.

Benefits & Perks

• Work remotely anywhere in Canada and/or access any of our hubs
• Health and dental benefits from day 1
• 4 weeks of paid vacation (including paid time off on your birthday)
• An additional 1 week of paid time off during the winter holidays
• Virtual & In-Person Social Events
• Annual Paid Volunteer Day Off
• 1:1 RRSP Matching Program Up to 3%
• $500 Pre-Tax Annual Health & Wellness Allowance
• $400 Pre-Tax Home Office Setup Allowance
• $65 Pre-Tax Monthly Phone Allowance
• Maternity and Parental Leave Top-Up Program
• Education Assistance Program
• Employee Referral Program
• Tenured Rewards Program

Salary Band: $90-100K CAD base salary per annum, plus a variable of $30-40K CAD, for an OTE of $120-140K CAD. Individual compensation will depend on unique skills, experience, and qualifications.

Vacancy Status: Existing vacancy

AI Use Disclosure: As part of our hiring process, we may use AI-powered tools to support tasks such as application screening and note-taking. These tools are used to assist our team, and all hiring decisions are made by humans.

We are committed to fair and unbiased hiring practices. If you require accommodations or have questions about how your application is assessed, please let us know.

At Makeship we are committed to fostering an environment that welcomes people of all backgrounds, experiences, and identities. We are passionate about building an equitable and inclusive culture for our unique and diverse team of employees which makes us Makeship. As an equal-opportunity employer, we value and embrace everyone's opinions and differences, and actively seek new Makeshippers who will work respectfully with our team, propelling our company and the community forward. If there are any accommodations we can provide to make your interview experience more accessible and inclusive, please let us know in your application.