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$200,000–$217,000/yr
Canada

  • Drive new business in the Mid-Market segment, owning the full sales cycle from prospecting to closing for companies with 50-175 trucks across Canada.
  • Meet or exceed monthly revenue quotas while maintaining high outbound lead generation through cold calling and strategic outreach.
  • Lead discovery calls, demos, and trials, and collaborate cross-functionally with Sales Development, Sales Engineering, and Account Management teams.

SaaS Outbound Sales Prospecting Negotiation

20 jobs similar to Mid Market Account Executive

Jobs ranked by similarity.

$85,887–$128,831/yr
Canada

  • Own the full outbound sales cycle from prospecting to close with mid-market merchants.
  • Build and manage a high-quality pipeline through cold outreach, social selling, and targeted campaigns.
  • Develop multi-product solutions across Square's ecosystem tailored to each merchant's needs.

Square provides omnichannel commerce and financial services tools to help sellers of all sizes run their businesses. As a subsidiary of Block, Inc., Square serves millions of sellers worldwide and fosters an inclusive culture.

$65,000–$70,000/yr
US 4w PTO

  • Own the full sales cycle for net-new mid-market customers, from outbound prospecting through close.
  • Lead consultative discovery and deliver tailored platform demonstrations to multi-stakeholder buyers.
  • Build and maintain a healthy pipeline using Salesforce, modern sales tech, and AI tools.

Muck Rack provides an AI-powered PR workflow platform that helps organizations manage media relationships, monitor news and social media, and measure impact. Founder-controlled and growing profitably, the company is fully distributed with an inclusive culture and serves thousands of organizations worldwide.

$80,000–$115,000/yr
US 4w PTO 16w maternity 4w paternity

  • Own the full sales cycle for mid-market accounts, sourcing and closing new business.
  • Conduct consultative sales and web demos to help organizations manage fleet operations.
  • Generate pipeline through outbound outreach and negotiate pricing to close opportunities.

Fleetio is a modern software platform that helps thousands of organizations worldwide manage fleet operations. The company raised $450M in Series D funding in March 2025 and fosters a collaborative, customer-centric culture with a driven sales team.

Global

  • Identify, develop, and close new business opportunities across mid-market accounts.
  • Own the full sales cycle from prospecting and qualification through negotiation and close.
  • Partner with BDRs, Solutions Engineers, and marketing to drive coordinated account engagement.

Mimica is an AI-powered process intelligence platform that helps enterprises identify bottlenecks, automate tasks, and reclaim time by turning work data into AI agents. The company is remote-first, globally distributed across 16+ countries, has raised $26 million in Series B funding, and is backed by investors like Khosla Ventures and Paladin Capital.

US Canada

  • Own a book of business from post-sale handoff through renewal and expansion, building strong mid-market customer relationships.
  • Identify expansion opportunities, conduct quarterly business reviews, and present tailored product demonstrations.
  • Manage pipeline and forecasting using Salesforce and other tools, with meticulous documentation and organization.

MaintainX is a mobile-first work execution platform helping industrial and frontline teams reduce downtime and run better operations. With more than 13,000 customers and now part of Autodesk, it's a fast-paced, high-growth environment focused on customer success.

$70,000–$90,000/yr
US Unlimited PTO

  • Own the full B2B SaaS sales cycle from prospecting to close.
  • Deliver tailored product demos and build relationships with EHS leaders.
  • Hit revenue targets using HubSpot, outbound prospecting, and referrals.

EHS Insight builds environmental, health and safety software used by over 1,000,000 people across 120+ countries. It is a fully remote, engineering-led SaaS company with a 4.7/5 G2 rating and a strong, supportive culture.

Canada

  • Drive revenue growth and exceed quarterly targets across the mid-market segment by owning the full sales cycle.
  • Prioritize new-logo acquisition while identifying expansion opportunities in strong product-fit accounts.
  • Engage security, IT, and business leaders in consultative cybersecurity conversations and close multi-stakeholder deals.

The company is a high-growth cybersecurity organization providing SaaS solutions to mid-market businesses. It fosters a supportive, collaborative culture that values respect, determination, integrity, and individual contribution.

Canada

  • Own the full sales cycle from prospecting and discovery to negotiation and close for commercial and mid-market accounts.
  • Combine hunting for new logos with farming a portfolio of approximately 40 existing accounts to drive retention and growth.
  • Engage technical buyers across engineering, DevOps, SRE, and IoT teams to deliver measurable revenue outcomes.

A technology partner offering open-source time-series data, observability, and monitoring solutions to commercial and mid-market organizations. The company operates in a globally distributed, collaborative culture that values ownership, continuous learning, and open-source principles.

  • Own full-cycle sales from prospecting to closing new logo accounts in the mid-market segment.
  • Prospect and manage your own pipeline using Salesforce, Outreach, and other tools.
  • Forecast monthly and quarterly sales with +/- 15% accuracy while juggling multiple tasks.

MaintainX is a mobile-first work execution platform for industrial and frontline teams. With more than 13,000 customers including Duracell, McDonald's, Shell, DHL and Volvo, it became part of Autodesk in 2026.

$95,000–$190,000/yr
Americas Unlimited PTO

  • Build and manage pipeline through self-sourced and SDR-supported leads to drive new customer acquisition.
  • Lead full-cycle sales from prospecting through demo and closing, focusing on mid-market accounts.
  • Conduct discovery calls to understand customer goals and position solutions effectively.

Customer.io helps over 9,000 companies send automated, behavior-driven messages like emails and push notifications. They value transparency and inclusion, with a growing team of over 200 employees and a culture centered on empathy, transparency, responsibility, and awkwardness.

Canada

  • Develop new and expansion sales opportunities with SMB fleets, managing leads and building pipeline through direct outreach and partner programs.
  • Conduct discovery calls, presentations, and demonstrations to align Geotab solutions with customer needs.
  • Maintain accurate opportunity data in Salesloft and Salesforce while collaborating with cross-functional teams to advance deals.

Geotab is a global leader in IoT and connected transportation, providing web-based fleet management analytics and an open platform. With a diverse, inclusive, and fast-paced culture, Geotab is certified as a Great Place to Work and processes billions of data points daily.

$129,600–$234,200/yr
US

  • Own the full outbound sales cycle for mid-market merchants, from prospecting to close.
  • Build and manage high-quality pipeline through cold outreach, social selling, and targeted campaigns.
  • Develop multi-product solutions across Square's ecosystem tailored to each merchant's unique needs.

Square provides integrated payments and software solutions for sellers of all sizes, enabling them to manage their entire business from one place. Block, the parent company, is a large publicly traded organization with a global team, fostering a culture of inclusion and fair opportunity.

$100,000–$120,000/yr
North America

  • Own new business with truck, construction and ag dealer groups of 5 to 30+ rooftops.
  • Run full-cycle sales from discovery to close on deals from $15K to $100K.
  • Collaborate with product, marketing, and dealer performance teams to win.

Trnsact builds a transaction operating system for commercial equipment, connecting dealers, lenders, OEMs, and protection providers on one platform. The company is cash-flow positive with about $3M ARR, serves customers like Penske and Ryder, and has a low churn rate.

US 3w PTO

  • Drive outbound growth by engaging decision-makers at multi-location auto repair groups.
  • Navigate complex organizations and build relationships with multiple stakeholders.
  • Master the product and employ consultative selling to tailor presentations to prospect needs.

Steer offers a suite of software tools for automotive repair shops, combining CRM, marketing, and scheduling solutions. The company is growing, having recently acquired AutoOps, and fosters a collaborative, high-ownership culture with opportunities for development.

US 4w PTO 16w maternity 4w paternity

  • Lead and mentor a team of Mid-Market Account Executives to accelerate performance and exceed revenue goals.
  • Own daily team operations including prospecting, funnel management, forecasting, and negotiation.
  • Collaborate with sales, marketing, and operations leaders to drive strategy and improve processes.

Fleetio is a modern software platform helping thousands of organizations manage fleet operations. The company is scaling rapidly after a $450M Series D and has been remote-friendly since 2012.

$56,250–$60,000/yr
Canada 3w PTO

  • Prospect via phone and email within your territory to drive pipeline growth using state-of-the-art tools.
  • Develop best-in-class outbound prospecting techniques to secure client meetings and demos.
  • Collaborate with Account Executives on market penetration and maintain meticulous CRM records.

Dealer-FX is a SaaS company that transforms dealership service lanes with innovative technology, backed by Snap-on Incorporated. It has a people-first culture focused on performance, collaboration, and work-life balance.

$109,500–$124,100/yr
Unlimited PTO

  • Lead and manage a team of Account Executives owning a defined segment of outbound sales across North American accounts.
  • Own segment-level pipeline, forecast accuracy, and monthly/quarterly MRR targets from top-of-funnel through close.
  • Hire, coach, and develop your team while optimizing sales processes with cross-functional partners to scale outbound motion.

We power businesses that are the backbone of the global economy with a one-stop cloud commerce platform. Founded in Montreal in 2005, we're a publicly traded company serving retail, hospitality, and golf businesses in over 100 countries.

US

  • Generate awareness and build pipeline by prospecting mid-market customers through outbound channels and following up on qualified inbound leads.
  • Qualify prospects, manage a portfolio of target accounts, and ensure seamless handoffs to Account Executives.
  • Partner closely with Mid-Market Sales and Marketing, reengage stalled opportunities, and contribute to team growth.

Lightcast is a global leader in labor market insights, providing data and solutions that drive economic prosperity and mobility. Headquartered in Moscow, ID, with offices worldwide, the company values diversity and encourages employees to bring their authentic selves to work.

US

  • Drive PAR's growth across the mid-market and SMB segment by promoting and selling unified commerce solutions.
  • Build relationships with decision-makers and stay current on industry trends to close deals.
  • Manage your sales pipeline and consistently achieve monthly targets.

PAR Technology Corporation is a leader in restaurant technology, providing software and hardware solutions to over 100,000 restaurants in more than 110 countries. They emphasize a "Better Together" ethos and focus on unified commerce, with a culture of collaboration and innovation.

$126,000–$180,000/yr
Global 16w maternity 16w paternity

  • Drive revenue growth by engaging prospects and expanding partnerships with commercial Docker products.
  • Achieve monthly and quarterly sales targets through sourced opportunities, accurate forecasting, and active client engagement.
  • Collaborate with cross-functional teams to share customer insights, inform product roadmaps, and drive marketing campaigns.

Docker is a leading developer tooling platform trusted by over 20 million monthly users and 20 billion container image pulls. We are a globally distributed, remote-first team that builds tools for building, sharing, and running applications, and we are at the center of the shift toward AI-agent-driven software development.