Strategic Account Executive

ContactMonkey Inc.; Toronto; Hybrid; CAD 225,000 - 250,000; Full time

Benefits offered by this job

Health benefits package

Work from anywhere up to 4 weeks

Stock option plan

RRSP savings plan

Generous vacation

Personal development budget

Birthday off

Job summary

ContactMonkey Inc. in Toronto is seeking a Strategic Account Executive to convert the Go-Get List into pipeline and revenue, reporting to the VP of Sales. You’ll multi-thread across parent organizations and align with CS, Marketing, and Product to drive expansion into whitespace.

You will own account mapping, forecast pipeline, and lead in a brand-new motion built from scratch. This replacement/new role offers a hybrid work model with generous benefits and a global remote option.

Qualifications

• 4+ years of full-cycle B2B SaaS sales experience, selling into mid-market or enterprise organizations.
• Proven track record of hitting or exceeding quota in expansion or land-and-expand motions.
• Comfort navigating multi-stakeholder deals with several buying centers and contacts per account.

Responsibilities

• Own and systematically work the Go-Get List in-ICP target business units, prioritizing by band, warmth, and renewal timing.
• Multi-thread every target account rather than relying on a single champion.
• Time outreach to parent-account renewal cycles to create natural, low-friction entry points into sibling business units.
• Deploy a full enablement stack per account, sequencing, proof-of-value packets, and executive sponsorship.
• Forecast and report on pipeline and bookings for opportunities.
• Collaborate with Marketing and Product to shape messaging and business cases for expansion-into-whitespace selling.

Skills

Full-cycle SaaS sales

Quota attainment

Multi-threading

Relationship-led selling

Tools

CRM

Job description

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About The Job - Strategic Account Executive

Join the Sales team in a net new position, where you’ll have the opportunity to capture a specific, quantified gap in how we grow inside our own customer base. Many of our existing customers are part of larger organizations: parent companies, holding groups, and franchise networks with sibling business units that ContactMonkey has never touched. We call this net-new whitespace our Go-Get List.

As our first Strategic Account Executive, you'll build and own the motion for converting the Go-Get List into pipeline and closed revenue, reporting directly to the VP of Sales. This is fundamentally a leverage-existing-relationships motion, you'll multi-thread into parent organizations, time outreach to renewal cycles, and work closely with Customer Success, Marketing, and Product to turn trust we've already earned into new business units and entities on the ContactMonkey platform.

What You'll Own

• Own and systematically work the Go-Get List in-ICP target business units, prioritizing by band, warmth, and renewal timing
• Multi-thread every target account rather than relying on a single champion, especially within larger operating-division targets
• Time outreach to parent-account renewal cycles to create natural, low-friction entry points into sibling business units
• Deploy a full enablement stack per account, sequencing, proof-of-value packets and executive sponsorship to build trust quickly
• Partner closely with the Account Management/CSM team on the strategic account list, focusing primarily on MM & Enterprise.
• Own organizational account mapping across your territory, researching corporate hierarchy, identifying decision-makers and champions at affiliated entities, and using existing ContactMonkey relationships to navigate into new buying centers
• Own forecasting and reporting on pipeline and bookings for opportunities
• Partner with Marketing and Product to shape messaging, collateral, and business cases specific to expansion-into-whitespace selling

What You Won't Own

• Upsell and expansion within accounts we already have: additional seats, modules, or add-ons for a business unit that's already a customer. This stays with our Account Management/CSM team
• Renewals, churn risk, and GDR on existing accounts are also owned by Account Management/CSM

About You

• You're a proven closer with 4+ years of full-cycle B2B SaaS sales experience, selling into mid-market or enterprise organizations
• A track record of hitting or exceeding quota in an expansion or land-and-expand motion, you know how to work an installed base, not just open new logos
• Comfort navigating multi-stakeholder deals with several buying centers and contacts per account
• A relationship-led seller skilled at warm-door selling using existing champions, with strong multi-threading instincts
• Experience with organizational account mapping, you can research corporate hierarchy, identify buying centers across subsidiaries and affiliated entities, and build pipeline where the org chart is your roadmap
• A systems-minded builder who's genuinely energized by building a brand-new motion from scratch versus inheriting an existing playbook
• Operates with a high degree of autonomy: you know when to loop in leadership and when to just handle it - you're comfortable navigating cross-functional relationships with CS, RevOps, Marketing, and Product without needing a warm handoff to get traction internally
• Highly collaborative and low-ego: quick to loop in CSM, Marketing, and Product, and you take ownership of outcomes, not just activity

How You Can Stand Out

• Experience with internal comms tools
• Experience selling into HR or Internal Comms teams

What We Bring to The Table

100% employer-paid benefits + a Health Spending Account from day one

Work from anywhere in the world for up to 4 weeks

Stock option plan—own a piece of our success

RRSP Group Savings Plan to plan for your future

Generous vacation package to recharge and relax

Personal development budget to fuel your growth

One personal day + two volunteering days to give back

Your Birthday off—celebrate on us!

Five health days per year to stay at your best

Beautiful downtown Toronto office for hybrid work—fully stocked with all the best snacks

Total targeted cash $225K-$250K ( base+ variable and draw on commission while you ramp). Compensation is thoughtfully determined based on your experience, skill set, and alignment with our internal compensation framework and internal equity.

We’re always happy to answer questions about compensation throughout the hiring process.

This is a (replacement/net new) position based out of our downtown Toronto office, at King and Spadina. Our team works in the office 3x per week to promote collaboration

Who We Are

Imagine being part of a team of brilliant minds, all shaping the future of workplace communication. Here at ContactMonkey, we’re not just sending out traditional emails with our internal comms software; we’re changing the way companies connect and communicate with their people. Brands like IKEA, Roku, KMPG, and countless others are using our solution to transform employee engagement.

Our all-in-one platform—featuring a drag-and-drop email builder, engagement tools, and analytics—makes it easy for businesses to create, send, and measure their internal email campaigns directly within Outlook or Gmail. This way, internal communications go from being ignored to binge-worthy, sparking more opens, clicks, and conversations.

We’ve been on an explosive growth streak over the past few years, and we’re not slowing down anytime soon. Here’s a bit of what we’re proud of:

• Ranked by the Globe & Mail as one of Canada’s fastest-growing companies
• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 50™ awards for revenue growth over the past four years
• Recognized in 2023, 2024 and 2025 Deloitte Technology Fast 500™ as one of the fastest-growing companies in North America
• Raised $55 million Series A financing in 2023

Diversity is Our Strength

At ContactMonkey, we are building diverse products and we need a diverse team to do that. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

We are committed to creating an accessible experience for all candidates. If you require any accommodations or adjustments during the interview process or beyond, please inform us, and we will work with you to ensure the necessary support is in place. We are continually striving to enhance our accessibility practices and welcome any feedback or suggestions on how we can better serve candidates with accessibility.

AI Disclosure:

We use AI to take notes during our interview. Applications and interviews are reviewed by our Talent Acquisition team. Our applicant tracking system utilizes AI for workflows and hiring process efficiencies.