Account Executive (Mid-Market)

About DashQ

At DashQ, we’re transforming how multi-family landlords lease apartments - making it as easy as booking a hotel room. We work with the largest and most innovative landlords in North America to automate the leasing process through a powerful combination of product, process, and people.

About the role

As an Account Executive (Mid-Market) at DashQ, you’ll own the full sales cycle - from outbound prospecting through close - for property operators and landlords across the mid-market segment.

This is a hands-on roll ideal for an AE who still loves prospecting (or a top-performing SDR who’s ready to step fully into closing). You’ll build a net-new pipeline, run discovery and demos, multi-thread deals, and close new business.

You won’t be doing it alone: you’ll be supported by a strong prospect pipeline out of the gate, a sales process that’s shortening as we scale, 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.

Target metrics:

• Annual new business quota: ~CA$800,000


• Typical ACV: ~CA$95,000 median (with meaningful CA$200,000+ deals)


• Sales cycle: ~3–6 months
  
  

Responsibilities

Pipeline generation & outbound execution

• Generate net-new qualified pipeline through multi-channel outbound (phone, email, LinkedIn, events, referrals, partner motions).


• Build account lists and outreach strategies by segment, persona, and trigger events.


• Consistently book and advance meetings through structured qualification and strong messaging.

Full-cycle sales ownership

• Own the end-to-end sales process: discovery, demo, value mapping, stakeholder alignment, proposal/negotiation, and close.


• Build compelling business cases and ROI narratives for property leadership teams (VP/Director/C-suite).


• Multi-thread deals across operational, financial, and technical stakeholders.


• Drive deal momentum using clear next steps, mutual action plans, and tight follow-up.

Cross-functional collaboration

• Partner closely with Implementation and Customer Success for smooth handoffs and fast time-to-value.


• Pull in DashQ’s technical and multifamily operator expertise to unblock deals, validate integrations/workflows, and strengthen customer confidence.


• Serve as the voice of the customer—sharing insights that improve product, messaging, and go-to-market strategy.

Operational rigor

• Maintain accurate pipeline hygiene, forecasting, and activity tracking in the CRM.


• Build and iterate playbooks, sequences, talk tracks, and objection handling as we scale.
  
  

About you

We’re looking for someone who is…

• Outbound-driven: you’re comfortable building your own pipeline and don’t rely on inbound to succeed.


• A strong communicator: you can earn trust quickly, ask sharp questions, and translate complex workflows into clear value.


• Structured and scrappy: you can follow a process, but you can also adapt fast and do what it takes to win.


• Coachability-first: you actively seek feedback, test improvements, and learn quickly.


• Motivated by ownership: you want a seat where you can shape the playbook—not just follow it.


• Energized by real-world operations: you like selling into teams that run real businesses and care about measurable outcomes.
  
  

Qualifications

• Experience in B2B SaaS sales with a consistent track record of performance, including outbound pipeline generation.


• Either:
  
  
  
  • 1+ years in a quota-carrying closing role (AE/ISR/Commercial AE), or
  
  
  • 12+ months as a top-performing SDR with repeated quota attainment and clear readiness to close full-cycle.
  
  
  
  


• Comfortable running 3–6 month deal cycles and managing multiple stakeholders.


• Strong sales fundamentals: discovery, qualification, objection handling, negotiation, follow-through.


• Experience using a CRM and outbound tools (e.g., Salesforce/HubSpot, Sales Navigator, sequencing tools) is a plus.


• Interest or experience in real estate, property management, or proptech is a plus (not required).
  
  

Why join

Growth and impact. It’s not often that you can get in on the ground floor of a funded startup that’s scaling. That means that instead of following a playbook, you’ll be writing it. Every day you’ll be challenged to improve how we sell, how we execute, and how we scale.

At DashQ, you’ll sell a product that matters to how housing operates - backed by a team that can help you win (technical depth + real multifamily operator expertise) and a pipeline that lets you get moving quickly.

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: $80,000 – $90,000
On-Target Earnings (OTE):$180,000

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.

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].