Account Executive

At Upland Software, you’ll find smart, creative teams who love working together to deliver value for our customers, and a global culture of growth and possibility. Our operating model has always supported remote work—and as we keep growing and evolving our workplace, that won’t change. We’re passionate. We’re proactive. We take pride in our work, and we love a good challenge. Sound like you? 

Professional services teams and global PMOs across North America often rely on spreadsheets and disconnected tools to manage projects, people, and budgets. That makes it hard for leaders to know what work matters most, whether projects are on track, and if they’re delivering real business value.

Upland PSA and PowerSteering help solve that problem. Our software gives organizations one clear place to plan work, manage resources, track financials, and show results—so teams can deliver projects on time, stay profitable, and confidently report outcomes to leadership.

As a Mid-market Account Executive, you’ll learn how to run real sales cycles, work with senior buyers, and close meaningful SaaS deals. You won’t be thrown in alone—you’ll be supported by experienced sales leaders and product experts as you grow into the role. This new role is designed for a high‑performing BDR or SDR who’s ready to take the next step into full‑cycle sales.

Base Salary range: $95,000-$105,000 CAD

Primary Responsibilities

Move into full‑cycle sales

• Own deals from sourcing through close, with coaching and support.
• Run discovery calls to understand customer challenges and goals.
• Build clear, simple business cases that show value and ROI.
• Present solutions to managers and executives in a confident, easy‑to‑understand way.
• Support pricing discussions and multi‑year SaaS agreements.

Build and manage pipeline

• Identify and develop new opportunities within assigned accounts and territories in a series of highly targeted sprints.
• Progress deals through a structured sales process.
• Maintain accurate pipeline, forecasts, and notes in CRM.
• Learn and apply enterprise qualification frameworks (e.g., MEDDICC / MEDDPICC).

Sell to real business buyers

• Engage leaders in professional services, PMOs, IT, finance, and operations.
• Learn how senior buyers think about priorities, budgets, and outcomes.
• Help customers connect day‑to‑day challenges to measurable business results.

Requirements

• 1–3+ years of experience as a BDR, SDR, or early‑career Account Executive in B2B SaaS.
• A strong desire to move into full‑cycle, quota‑carrying enterprise sales.
• Comfortable speaking with customers and asking thoughtful, business‑focused questions.
• Coachable, curious, and motivated to improve every quarter.
• Organized and able to manage multiple opportunities at once.

Desired Skills

• Exposure to enterprise or mid‑market customers.
• Experience supporting longer or more complex sales cycles.
• Familiarity with professional services delivery, project management, or PMO environments.
• Interest in value‑based selling (business outcomes, ROI, efficiency).
• Completion of a structured sales certification program (e.g., MEDDICC, Challenger, SPIN, Sandler, or similar) is strongly encouraged.

Upland Software is an Equal Employment Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status or other legally protected status.