Enterprise Account Executive selling CharterUP’s AI - powered group transportation platform to large organizations. Owning complex sales cycles, RFPs, MSAs, and enterprise revenue growth.
About the role
- Account Executive (Mid-Market) at DashQ managing the full sales cycle for multi-family owners in North America. Generating qualified pipelines, guiding discoveries, and closing deals in a fast-paced startup environment.
Responsibilities
- Generate net-new qualified pipeline through multi-channel outbound (phone, email, LinkedIn, events, referrals, partners).
- Run discovery, demos, and value mapping with VP/Director/C‑suite stakeholders - connecting DashQ to operational and financial outcomes.
- Own the deal end-to-end: qualification, multi-threading, proposals, negotiation, and close.
- Attend industry conferences to increase market presence of DashQ in Canada and abroad.
- Build and manage a healthy pipeline with accurate forecasting and crisp next steps (mutual action plans, timelines, stakeholders).
- Partner with Implementation and Customer Success for smooth handoffs and fast time-to-value; identify expansion paths over time.
- Bring customer insights back to the business - helping improve messaging, playbooks, and product direction as we scale.
Requirements
- 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).
Benefits
- 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.
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