Matcha

260 Remote Sales Jobs in Canada

260 remote sales roles open to candidates in Canada, all at fully remote, VC-backed startups from seed to series C. Matcha reads every job description daily and sends you one zero noise email with only the roles that really fit. No scrolling, no noise.

10k+ under the radar remote startups · 1 zero noise email

Describe your next role, cut the noise

260 open roles · 16 new this week · 80% not on LinkedIn · $174K avg pay

  • Ashby logo

    Mid-Market Solutions Engineering Manager at Ashby

    Building people software for high growth companies.

    Team of 489Mid-level$141.6MHuman ResourcesSoftwaresolutions engineeringteam leadershipsaas sales$210K–$280K / yearBacked by Lachy Groom, Alkeon Capital, F-Prime

    You will lead and grow a high-performing team of Solutions Engineers to support mid-market sales motions and drive revenue. This involves coaching team members, operationalizing sales processes, and partnering with sales leadership to ensure technical and commercial success.

    Remote US and Canada. Lead Solutions Engineering team supporting sales motions; no other region restrictions stated.

  • Strada logo

    Enterprise Account Executive at Strada

    AI-native insurance ops platform automating customer interactions across channels.

    Mid-levelSeed · $4.25MData IntegrationSoftwareenterprise salesb2b salesconsultative selling$240K–$320K / yearBacked by Y Combinator

    Own the end-to-end sales process to drive new business with insurance carriers, brokers, and TPAs. Act as a trusted advisor to guide customers from manual operations to AI automation while collaborating with product teams on the roadmap.

    Remote regions not specified; position appears open broadly without geographic restrictions.

  • Swiftly, Inc. logo

    Solutions Engineer at Swiftly, Inc.

    Leading real-time transit data platform improving reliability and ridership.

    Team of 143Mid-level$27.2M Private EquityReal TimeE-Commerceproduct demossales strategytechnical translation$120K–$155K / yearBacked by JMI Equity, Cove Hill Partners

    The Solutions Engineer will lead product demonstrations, develop sales strategies, and provide technical expertise to help transit agencies understand the value of Swiftly's platform. They will also manage pilot programs, organize onsite workshops, and act as a bridge between prospective customers and internal product teams.

    Remote US and Canada (Ontario, British Columbia). No visa sponsorship.

  • 1mind logo

    Enterprise Account Executive at 1mind

    Redesigning digital therapy with 800+ therapists to empower clients.

    Team of 6Mid-levelSeries A · $40Msaas salesoutbound salespipeline building$125K–$160K / yearBacked by Battery Ventures, Neeraj Agrawal, Brandon Gleklen

    You will manage the full sales cycle from outbound prospecting to closing deals with enterprise-level clients. Additionally, you will act as a thought leader to evangelize AI-led revenue growth and partner with leadership to refine sales strategies.

    Remote US and Canada. Remote-first; expect up to ~30% in-market travel for customer meetings/events.

  • 83 Sciences logo

    Head of Sales / Founding GTM at 83 Sciences

    AI-driven engine powering research and materials discovery.

    Director$2.1M total fundingenterprise salestechnical salespipeline building$170K–$220K / yearBacked by Alchemist Accelerator, European Network of AI Excellence Centres

    Own the full sales cycle from prospecting to closing, focusing on converting scientific exploration contracts into long-term manufacturing partnerships. Develop the GTM playbook and eventually recruit and lead the sales team as the company scales.

  • PermitFlow logo

    Enterprise Account Executive - Commercial & National Accounts at PermitFlow

    Construction's AI Workforce

    Mid-levelSeries A · $31MConstructionAppsenterprise salesstrategic account managementcomplex deal negotiation$300K–$350K / yearBacked by Accel, Initialized Capital, Kleiner Perkins

    Own the full sales cycle for strategic national accounts, focusing on acquiring new enterprise logos and expanding existing partnerships. Develop ROI-driven business cases to convert pilots into portfolio-wide rollouts for large-scale developers and retailers.

    Remote eligibility not specified; likely based in the US with travel for customer meetings, conferences, and kickoffs.

  • Resend logo

    Technical Account Executive at Resend

    Developer-focused email platform and tools.

    Team of 75Mid-level$21.5MInformation TechnologyEmailsalesaccount managementtechnical sales$160K–$220K / yearBacked by Y Combinator

    The Technical Account Executive will manage high-intent inbound opportunities and iterate on sales playbooks to scale the company's repeatable sales motion. They will also focus on expanding existing customer accounts and preventing churn by acting as the voice of the customer internally.

    Remote in Americas time zones; flexible schedule. Americas-based; may include worldwide remote per Americas locations wording.

  • Job Board logo

    Regional Vice President, Sales - West at Job Board

    Transforms network data into definitive AI-evidence for expert SOC workflows.

    Team of 473Executive$309.2M total fundingHealth DiagnosticsHealth Caresales strategyteam leadershiprevenue growth$400K–$520K / yearBacked by Accel, Insight Partners, General Catalyst

    Lead and develop a high-performing team of Enterprise and Strategic Account Executives to drive regional revenue growth. Define regional sales strategies, manage pipeline performance, and build executive-level relationships with key security stakeholders.

    Remote North America (US/Canada). Regional West sales leadership; travel within assigned region required.

  • Job Board logo

    Strategic Account Executive - NA WEST at Job Board

    Transforms network data into definitive AI-evidence for expert SOC workflows.

    Team of 477Mid-level$309.2M total fundingHealth DiagnosticsHealth Careenterprise software salescybersecuritycloud infrastructure$339K–$410K / yearBacked by Accel, Insight Partners, General Catalyst

    The Account Executive will own and grow a defined geographic territory by developing strategic account plans and driving sales into enterprise customers. They will lead complex sales cycles, build relationships with security leadership, and partner with cross-functional teams to achieve sales targets.

    Remote North America (West territory); locations in US or Canada.

  • Spellbook logo

    Manager, Mid-Market Customer Success at Spellbook

    AI suite for commercial lawyers, trusted by 4,000+ teams worldwide.

    Team of 233Mid-level$82.4M Total FundingSportsGamingcustomer success managementteam leadershipcoachingC$125K–C$145K / yearBacked by Moxxie Ventures, RBC, Chicago Ventures

    The Manager will lead, coach, and scale a team of Mid-Market Customer Success Managers to drive adoption, retention, and renewal outcomes. They will also build and refine internal processes, playbooks, and reporting structures to ensure consistent team performance.

    Remote in Canada only; distributed startup role with weekly coaching and renewals/forecasting responsibilities.

  • Jerry.ai logo

    Director, Business Development & Partnerships at Jerry.ai

    Jerry is America's first and only AllCar™ app, on a mission to make car ownership affordable and accessible.

    Team of 399Director$381.1MSoftwareInsurTechbusiness developmentpartnership managementstrategic consulting$180K–$220K / yearBacked by Goodwater Capital, Park West Asset Management, TriplePoint Capital

    You will own the end-to-end partnership motion for new product lines, including building the pipeline, structuring complex deals, and ensuring partner success. You will also contribute to vertical strategy by leveraging your ground-level view of partner requirements to guide product development.

    Remote within AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA and Ontario (Canada). Not elsewhere.

  • ThoughtExchange logo

    Account Executive at ThoughtExchange

    K-12 strategic insights platform turning community voice into decisions.

    Team of 130Mid-level$13.5M Venture RoundCommunitiesQ&Afull-cycle salessaasoutbound prospectingC$163K–C$182K / yearBacked by InBC Investment, Yaletown Partners, Information Venture Partners

    The Account Executive is responsible for creating, leading, and closing new sales opportunities while managing a robust pipeline within an assigned territory. They will collaborate with internal teams to develop territory strategies, navigate complex procurement processes, and represent the company at industry events.

    Remote-first; work from Canada or the United States. No other location restrictions stated.

  • UserGems logo

    VP of Sales at UserGems

    AI-driven sales and marketing command center boosting pipeline and revenue.

    Team of 106Director$22.4M total fundingArtificial IntelligencePredictive Analyticsteam leadershipsales coachingfull cycle sales$250K–$350K / yearBacked by Uncork Capital, Craft Ventures

    The VP of Sales will lead, coach, and scale the full-cycle sales team while driving revenue predictability and pipeline health. They will act as a player-coach, engaging in strategic deals and collaborating with marketing to align on revenue goals.

    Remote-first; role open across Americas and Europe (includes US/Canada, likely LATAM, and EU).

  • Tailscale logo

    Solutions Engineer - Commercial (Expansion Sales) at Tailscale

    Easy, secure private networks; no upfront cost, minimal latency.

    Team of 343Mid-level$436.9M total fundingInformation TechnologyCyber Securitynetworkingsecurity softwaretcp/ipC$201K–C$268K / yearBacked by Accel, Heavybit, Insight Partners

    Partner with Account Executives to drive new business by leading technical discovery, solution architecture, and product demonstrations. Build scalable enablement resources and provide structured feedback to influence the product roadmap and go-to-market strategy.

    Remote Canada. Canada-based candidates only; no other regions specified.

  • Cursor logo

    Regional Director, SLED at Cursor

    Builds AI developer tools to automate coding for programmers.

    Director$3.3732B total funding$161K–$229K / yearBacked by Thrive, Accel, Andreessen Horowitz

    Build, hire, and lead a team of SLED Account Executives in the region

    Remote worldwide.

  • Cursor logo

    Commercial Account Executive at Cursor

    Automates coding with an AI tool for professional programmers.

    Mid-level$3.3732B total funding$195K–$195K / yearBacked by Thrive, Accel, Andreessen Horowitz

    Win new business and drive Cursor revenue by owning the full sales cycle from first call to close

    Remote with no stated regional restrictions.

+244 more sales roles in Canada

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About Matcha

Matcha is a zero-noise alternative to job boards for remote startup jobs. Instead of scrolling through hundreds of irrelevant postings, you describe your next role once and Matcha reads every job description daily to surface only the roles that actually fit. Matches arrive in a single email, as soon as a relevant role is posted. No UI to check, no notifications, no noise. Because Matcha reads full job descriptions in plain language, there is no limit to what you can filter by: not just the usual dropdowns, but anything you can put into words.

Matcha surfaces fully remote jobs at startups from seed to series A, series B, etc. typically backed by top-tier VCs like a16z, Index Ventures, Y Combinator, Google Ventures, Sequoia, Accel, Khosla Ventures, etc. Roles span software engineering, design, marketing, sales, and more. Open to candidates in Europe, the US, Canada, the UK, Brazil, Latam, APAC, and worldwide.

Frequently asked questions

Job boards make you scroll through hundreds of irrelevant posts. Matcha flips this: you describe your ideal role once (title, tech stack, team size, dealbreakers) and Matcha reads every job description daily to surface the handful that actually fit, and sends you one zero noise email. No UI to check, no noise, just a single email when something real shows up. Unlike job boards with their fixed filter sets, Matcha uses plain-language descriptions to match against full job descriptions, so you can filter by anything, something no dropdown could ever capture.

You describe what you're looking for in plain language: role, tech stack, team size, things you don't want. Every day, Matcha scans thousands of new remote startup job postings and compares each description against your preferences. Roles that match land in your inbox in a single, zero-noise email within hours of being posted.

Roles are added as soon as they are posted. About 80% of them never appear on LinkedIn.

Yes, all public jobs are covered: workatastartup (YC jobs), Ashby, Greenhouse, and more. Matcha also tracks under-the-radar startups individually, including roles that are not listed anywhere else.

Matcha was built by Fico, a Canadian repeat founder who has spent over a decade building and working at fully distributed startups. He was on the founding team of Roger.ai, a fully distributed startup he helped grow from zero to $5 billion in transaction volume and millions in ARR before it was acquired by NYSE:CPAY, where he served as VP of Engineering for four years, fully remote. Fico has a deep network of remote-first founders and understands this space firsthand.

While looking for a new startup to join, Fico found the experience exhausting: noisy job boards, limited filters, and no way to specify what actually mattered to him. Nothing let him filter the way he wanted. So he built it for himself, shared it with friends, and after seeing how much they loved it, opened it up. The goal: stay open to the right opportunity without the daily grind of checking boards or wading through noise. It takes two minutes over coffee instead of hours.

Loved by 3000+ remote talent

Engineers, PMs, designers, and marketers across 40+ countries use Matcha to cut through the noise of job search and not miss the right opportunity when it's posted.

Describe your next role, cut the noise