Head of Partnerships

The Leadership Agency; Toronto; On-site; CAD 150,000 - 210,000; Full time

Benefits offered by this job

Meaningful equity

30 days PTO

Health and dental

Parental leave top-up

Tech allowance

Home service allowance

Wellness spending account

Job summary

Quartermaster, a Toronto-based home services marketplace, seeks a leader for the Pro side to own acquisition, activation, engagement, and long-term success. You will build a value equation Pros can’t refuse and scale the system, reporting to the CEO and acting as a peer to product leaders.

Expect to lead a ~10-person team, drive cross-functional impact, and shape a citywide growth plan as the platform rebuild advances in 2026. On-site in downtown Toronto with equity-backed compensation.

Qualifications

• 8+ years in tech sales, partnerships or marketplace supply leadership.
• Proven track record building a function from the ground up.
• Deep exposure to SMB, blue-collar or trades customers.
• Comfortable with principles and outcomes over narrow targets.
• Systems thinker who can design automated funnels, not just relationship-led motion.
• Credible as a peer to product leaders on strategy and communication.
• Player-coach instinct for field and leadership.
• Genuine startup intensity with judicious prioritization.

Responsibilities

• Own the full Pro-side strategy from acquisition to retention and scaling.
• Lead acquisition as a scalable system with automated funnels.
• Partner on referral activation and ensure high-quality Pro supply.
• Coach and grow a team of ~10 across two functions and align with product leaders.
• Shape org design for 3-, 6-, 9-month horizons and drive execution across Pro lifecycle.

Skills

Tech sales leadership

Partnerships leadership

Marketplace supply leadership

Build a function from scratch

SMB/blue-collar exposure

Systems thinking

Automated funnels / CRM

Product peer collaboration

Startup pace

Job description

Quartermaster is a Toronto-built home services marketplace where every Pro is referred by a verified neighbour before they can be booked. Homeowners find local Pros, request quotes, manage bookings and documents, pay in-app, and pass their own referral down the street — all from one platform. It's word of mouth, turned into infrastructure.

The model is a deliberate rejection of how the category works. Most platforms sell the same lead to four contractors or take 20–30% of every job, which pushes the best Pros off the platform entirely. Quartermaster runs on low commissions and neighbour referrals, backed by a Good neighbour Guarantee that puts up to $2,500 behind every job. The result is a marketplace the city's most trusted Pros will actually say yes to.

Founded in 2015, Quartermaster has spent a decade assembling the pieces required for a genuine city-scale marketplace: network density, Pro supply, and a product good enough to compound. A two-year platform rebuild is now landing, and the company is heading into the most consequential stretch of its life — a run at building the first low-commission, citywide home services utility in North America.

Highlights

• Founded 2015, HQ in Toronto
• 89 employees, up 34% year over year
• Every Pro on the platform is referred by a verified homeowner — no paid placements, no shared leads
• Good Neighbour Guarantee backs every job up to $2,500
• Field canvassing converts 20–30% of homes in a targeted neighbourhood
• Two-year platform rebuild completing in 2026, with a new consumer product rolling out through the fall

About the Role

This is the leadership seat over the entire Pro side of Quartermaster's marketplace — acquisition, activation, engagement, and long-term success. It exists because the Pro funnel is the constraint on everything: without deep, high-quality Pro supply, the homeowner experience doesn't work and the network doesn't compound.

Your job is to build a value equation Pros can't say no to, and a system that delivers it at scale. You'll report directly to Michael Phillips, Co-Founder and CEO, and operate as a true peer to the product leaders building alongside you.

Please note: this role is currently on-site in downtown Toronto.

Strategy & Marketplace Thinking:

• Own the full Pro-side strategy — acquisition through retention, and the work-back plan to get from today's volume to citywide scale
• Interrogate the conversion metrics the team runs on: which ones actually extrapolate to marketplace success, and which are comfortable but meaningless
• Model how Pro-side outcomes interconnect with homeowner acquisition, product releases, and marketplace liquidity
• Bring a top-down strategic lens to the team, and level them up in the process
• Lead the acquisition team calling, demoing and vetting Pros moving from free visibility to bookable, paying marketplace participants
• Rebuild acquisition as a scalable system rather than a headcount-led motion — automated funnels that drive the right engagement and the right buy-in
• Partner on the referral activation function upstream, where neighbour referrals collected in the field convert into verified Pros on the platform
• Shape how the acquisition and activation functions should be structured as the funnel matures

Pro Success & Retention:

• Own the accounts team driving Pro engagement, performance and long-term success on the marketplace
• Solve for the right yeses: a Pro who signs up must still be glad they did six months later, and want to double down
• Build the pitch and the systems that bring high-frequency maintenance Pros to move their existing book onto the platform
• Integrate acquisition and accounts into one coherent lifecycle rather than two handoffs

Team & Cross-Functional Leadership:

• Lead, coach and grow a team of roughly ten across two functions, with a high bar on intensity and standards
• Act as a genuine peer to product managers — strategy, critical thinking, and thought leadership, not just requirements handoffs
• Build the culture: this is a team that has run on competitiveness and commitment, and needs a leader who reinforces it
• Own the plan for what the org should look like at three, six and nine months out

About You

The person who wins this role has built something from scratch before. They're commercially sharp but not a pure closer — they think about what happens to a Pro six months after the yes, not just whether the yes lands. They can sit across from a product leader and argue strategy, then go out and run a field team. And they want an early-stage marketplace at a decisive moment, not a polished org where the playbook is already written.

• 8+ years in tech sales, partnerships or marketplace supply leadership, including real experience managing and developing teams
• Proven track record building a function rather than inheriting one — the CRM, the process and the team didn't exist when you arrived
• Deep exposure to SMB, blue-collar or trades customers, and a clear-eyed understanding that earning trust in that market is most of the job
• Comfortable being handed principles and outcomes instead of narrow targets, and building the path yourself
• Systems thinker who can design an automated funnel, not just run a relationship-led motion
• Credible as a peer to product leaders on strategy, critical thinking and communication
• Player-coach instinct — as useful in the detail and in front of Pros as in the leadership meeting
• Genuine startup intensity, with the judgment to know where the effort should go

Bonus:

• Two-sided marketplace experience, specifically on the supply side
• Launched or scaled a city, or run city-by-city growth
• Home services, field services or trades-adjacent background

The Extras that Matter

• Meaningful equity — Quartermaster holds 50% of fully diluted shares in its employee option pool and deliberately spreads ownership rather than concentrating it in a handful of executives
• Best-offer-first compensation philosophy: no negotiating games, no one paid according to how hard they pushed
• 30 days of PTO, including five company-wide closure days so the whole team switches off together
• Comprehensive health and dental coverage for you and your family
• 100% parental leave top-up, plus $1,000
• Tech allowance to upgrade your laptop
• Home service allowance, spent through the Qm app
• $1,200 wellness spending account
• Direct reporting line to the CEO, with real influence over how the Pro organization is structured
• A downtown Toronto office and a team that genuinely works in the same room