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Head of Sales in Montréal, Quebec at Planned

NewEmployment Type: Full-Time
Planned
Montréal, Quebec, Canada
Posted on
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Job Description

Planned is the AI Event Intelligence Platform. Enterprises use Planned to source, manage, and pay for their meetings and events, with AI doing the work that used to take entire teams and agencies. We're about 75 people, headquartered in Montreal, going after one of the largest categories in B2B that software never properly captured.

We're on a mission to disrupt a $500+ billion industry. To achieve that, we want to work with brilliant minds and natural leaders who are driven to out-think, out-plan, and outperform the competition. We tackle every business decision with enthusiasm, and we love the work that we do!

As our Head of Sales, you'll own revenue at Planned - the number, the team, and the machine that takes us to our next order of magnitude. Founder-led sales got us here, with strong logos and a motion that works. Your job is to industrialize it without slowing it down. The deals are real enterprise sales: seven- to nine-figure deals, multi-stakeholder cycles, procurement and security reviews, and incumbents defending their renewals. You'll work directly with the founders on the biggest deals and the GTM strategy behind them.


What You'll Do
  • Own new ARR: pipeline coverage, conversion, forecast accuracy, and ultimately the number itself.
  • Hire, ramp, and coach a team of enterprise AEs who can run seven- to nine-figure, multi-threaded cycles.
  • Codify the playbook from founder-led wins into a repeatable motion: discovery, demo, business case, procurement, security, close.
  • Build the displacement motion against the legacy incumbents: timing renewals, building switch cases, and de-risking the move for buyers.
  • Design the land-and-expand path from a first event or program to full platform deployment across an enterprise.
  • Install operating rigour: stage definitions, CRM hygiene, weekly forecast, and win/loss reviews that actually change behaviour.
  • Partner with Marketing on pipeline generation and with Customer Success on expansion revenue.
  • Stay in deals yourself. You'll personally help land the lighthouse logos that define each year.


What We're Looking For
  • Enterprise SaaS sales leadership at a high-growth company, with personal and team success closing $500K+ ACV deals.
  • You've scaled revenue through the $10M to $100M stage and know what breaks at each step.
  • Player-coach DNA: you build systems and teams, but you still love being in the room.
  • Forecast credibility: your number is real, and your pipeline reviews make reps better, not defensive.
  • Experience winning competitive displacement deals against entrenched incumbents.
  • You've built outbound pipeline, not just worked inbound. You and your team know how to create demand, not just close it.
  • AI tools are a natural part of how you and your team sell, not an afterthought.
  • High agency, low ego, fast. You create urgency without creating chaos.


What Makes You Stand Out
  • You've sold into events, travel, procurement, or corporate services buyers.
  • You've competed directly against the category's legacy software or agency players.
  • Experience selling platforms that replace both software and services spend.
  • You've built partner- and channel-sourced pipeline.

About the Team
  • Building the AI-native operating system for corporate event management and procurement.
  • Trusted by companies like OpenAI, Discord, Coinbase, LEGO, DoorDash, and EY, and is replacing the legacy software and agencies that have run corporate events for decades.
  • Scaling aggressively over the next two years.
  • Selling seven- to nine-figure platform deals to some of the most demanding enterprise buyers in the world.
  • Using AI tools as a natural part of how we sell: research, prep, follow-up, enablement.
  • Living three values: Bias to action. Care deeply. In the trenches together.


What We Offer
  • Culture of high performance, strong talent density and in-person collaboration
  • Unlimited PTO
  • Competitive comp packages
  • All the tools and gear you need to be successful (Macbook, screens, mouse, keyboard, Claude, etc.)
  • Health, dental, vision, and psychology insurance
  • Bus pass subsidy or indoor parking
  • Stocked up snacks & lunches in office 2x per week
  • Dog-friendly office
  • Relocation support, if needed

Job Location

Montréal, Quebec, Canada

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