Account Executive (Enterprise)

About DashQ

Everyone needs a place to live, but renting is still full of friction—for renters and onsite teams. DashQ helps large multi-family owners and operators bring AI to the entire renter lifecycle and automate the workflows property teams run every day, so leasing happens faster, with less manual work, and a better experience for everyone.

We partner with some of the largest and most innovative multi-family owners and operators in North America to reimagine the people, process, and technology behind leasing—so teams can move faster, operate with consistency, and deliver a better resident experience.

About the role

As an Enterprise Account Executive at DashQ, you’ll own the full sales cycle—from strategic outbound prospecting through close—for institutional multi-family owners and operators with complex operating environments and multi-stakeholder buying committees.

This is a high-ownership role for an enterprise seller who can build and execute account plans, create executive alignment, and navigate procurement, legal, and technical evaluation to win large, multi-year deals. You’ll work closely with Customer Success and Implementation to drive successful rollouts and identify expansion opportunities over time.

You won’t be doing it alone: you’ll be supported by strong coverage, a sharpening sales process, and an internal bench of technical experts and experienced multifamily operators who can jump in to accelerate deal cycles, de-risk technical validation, and help customers connect DashQ to real operational outcomes.

• ~3× YoY growth + well-funded with meaningful equity (unicorn-scale ambition)


• High-ACV, multi-year deals + consistently strong attainment


• Strong coverage/pipeline + deep technical and multifamily operator support to help you win
  
  

We hire the best, expect the best, and give our best every day. If the thought of working at an intense pace in pursuit of building something massive excites you, this is the team to join.

How success is measured (typical)

• Annual new business quota: ~CA$1.2M–CA$2.0M (segment dependent)


• Typical ACV: ~CA$250k–CA$500k+, with meaningful multi-year expansion potential


• Sales cycle: ~4–10 months (enterprise evaluation, procurement, rollout planning)
  
  

What you’ll do

• Build and execute strategic account plans across a focused set of named enterprise accounts.


• Generate and progress net-new pipeline through account-based outbound (phone, email, LinkedIn, events, partners), leveraging trigger events and stakeholder mapping.


• Lead discovery, demos, and value mapping with executive stakeholders (COO/CFO/CIO/EVP/VP level), tying DashQ to operational and financial outcomes.


• Own complex, multi-threaded deals end-to-end: qualification, mutual action plans, technical validation, procurement/legal/security reviews, negotiation, and close.


• Partner tightly with Implementation and Customer Success to ensure smooth handoffs, phased rollouts, and long-term expansion opportunities.


• Represent DashQ at key industry conferences and executive events to deepen enterprise relationships and market presence.


• Bring customer insights back to the business to strengthen messaging, playbooks, and product direction as we scale.
  
  

About you

You’re hungry, driven, and ready to build something massive.

• You have strong executive presence and can earn credibility quickly with senior leaders.


• You thrive in complex, multi-stakeholder environments and know how to create alignment and urgency.


• You’re structured, accountable, and disciplined with pipeline, forecasting, and next steps.


• You’re collaborative and know how to run a deal team (technical, operator, CS, leadership).


• You’re coachable and always sharpening your craft.
  
  

Qualifications

• 5+ years quota-carrying closing experience in B2B SaaS (enterprise and/or strategic accounts).


• Proven success selling into complex orgs with procurement, legal, and multi-threaded stakeholder groups.


• Experience carrying and hitting a meaningful quota (of CA$1.25M+ new business), or a track record of closing deals with enterprise-level ACV and complexity.


• Strong sales fundamentals (discovery, qualification, negotiation, follow-through); familiarity with MEDDICC / mutual action plans is a plus.


• CRM proficiency and strong operational rigor (forecasting accuracy, pipeline hygiene).


• Experience in real estate, property management, proptech, or adjacent workflow/ops software is a plus (not required).


• Willingness to travel for key customer meetings and industry events.
  
  

Benefits

In addition to the growth and impact you’ll have at DashQ, we offer competitive compensation along with:

• Equity in the company in the form of stock options


• Health, dental, and vision


• Fun company social events


• Personal development support


• Relocation packages for those who live outside Ontario - we’ll make the move exciting, not painful.
  
  

Job Compensation Range

Base Salary Range: $125,000 – $145,000
On-Target Earnings (OTE):$280,000

DashQ offers a competitive total rewards package which includes base salary, equity, a comprehensive benefits & perks package, and commission. Exact compensation is determined based on a number of factors including experience, skill level, location and qualifications which are assessed during the interview process. Additional details about total compensation and benefits will be provided during the hiring process.

DashQ provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristics protected by federal, provincial or local laws. 

If you need assistance and/or a reasonable accommodation in the application or recruiting process due to a disability, please contact us at [email protected].