Enterprise Account Executive

Pogo Technologies, Inc.; Canada; On-site; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Unlimited PTO

Minimum 20 days vacation

Job summary

Pogo Technologies, Inc. is seeking an Account Executive to scale our B2B enterprise business in Canada. You will own the full sales process from prospecting to expansion, building relationships with senior stakeholders and delivering ROI-focused outcomes.

You will drive trials, coordinate POCs, negotiate with customers, and partner with founders on strategy. This role requires a hunter mindset, strong communication, and the ability to move quickly in a growing startup environment.

Qualifications

• 3–10 years of enterprise sales experience.
• Strong communicator with senior stakeholders.
• Hunter mindset with ownership of targets.

Responsibilities

• Own the full sales cycle from prospecting to expansion.
• Lead generation across outbound email, calls, conferences, and referrals.
• Coordinate trials and POCs end-to-end to accelerate closing.
• Drive renewals and upsell opportunities within accounts.
• Collaborate with GTM, Engineering and Product teams to set up customers for success.
• Travel up to 3–5 days per month.

Job description

About your role

We’re hiring our first AEs at Pogo to help us scale our B2B enterprise business from $XM ARR to $XXM ARR. You'll own the full sales cycle from prospecting to expansion.

Specifically, you will:

• Lead generation & engagement: get Pogo in front of the right people by building relationships with prospects across outbound email, calls, conferences, and dinners. Stay on top of inbound and referral leads and keep pipeline moving.
• Qualification & closing: lead discovery, demos, and follow-up conversations to understand prospect needs and close new business. Build compelling ROI cases and navigate contract negotiations to get deals over the line.
• Consultative selling with trials & POCs: own the trial experience end-to-end, coordinating with other Pogo team members to ensure every project is successful and accelerates the path to closing a subscription.
• Renewals & expansion: own the renewal cycle for your accounts and actively identify upsell and cross-sell opportunities. Build deep relationships with existing clients to understand their evolving needs and grow revenue within the base.
• Process & feedback: help build and improve the sales playbook as we scale. Bring structured learnings back to the team and contribute to a culture of rapid iteration on what's working.
• Travel up to 3-5 days a month.
• Cross-team collaboration: work closely with GTM, Engineering and Product team members to make sure new clients are set up for success from day one. Partner with the founding team on strategic deals and revenue priorities.

About you

• Likely 3-10 years of sales experience, including selling to enterprise customers end-to-end
• You're a hunter. You're energized by building pipeline from scratch and you don't wait for leads to come to you.
• You're a strong communicator who can earn credibility quickly with senior stakeholders and translate a product demo into a compelling business case.
• You're hands‑on and resourceful. You do whatever it takes to get a deal across the line.
• You take ownership of your number. You know where you stand at all times and you're always working the problem.
• You're a fast learner who picks up new products, industries, and buyer personas quickly.
• You're a key user of AI tools to work smarter and to do better research, better outreach, better prep.
• Bonus:
  • You can tell stories with data.
  • You have sold insights or data analytics products

Why you might be excited about this opportunity

• Help build the GTM motion from the ground up. You won’t just be joining a sales team - you’ll help define how we sell, who we sell to, and what great looks like as we scale.
• Sell a product customers genuinely want. We’re seeing strong inbound interest from the largest consumer brands in the world, and you’ll work closely with prospects who are excited about using Pogo's products to accelerate consumer insights, sales, marketing, etc.
• Work directly with the founders and product team. As one of our first AEs, you’ll have a direct line into company strategy, pricing, positioning, and roadmap decisions. Customer feedback from your conversations will shape both the product and the business.
• Operate with fast feedback loops. We move quickly, iterate constantly, and care deeply about learning. You’ll be able to test messaging, refine outreach, and influence product direction in days - not quarters.
• Own meaningful customer relationships. From first outbound touch to closed-won and expansion opportunities, you’ll have real ownership over accounts and the ability to become a trusted partner to customers.
• Join a highly product‑minded team. Everyone at Pogo - from engineering to GTM - obsesses over building useful, delightful products. We care deeply about craft, customer empathy, and creating experiences people love.
• Shape the culture early. As an early team member, your approach to sales, collaboration, and customer relationships will help define the culture and playbook for future hires.

Why you might not be excited about us

• There’s very little structure (yet). As one of our early GTM hires, you will be expected to work with your teammates, Founders, Growth team, and Marketing team to develop playbooks and build the foundations as we scale.
• You’ll need to thrive in ambiguity. Enterprise sales at Pogo often means navigating new buyer personas, shaping positioning in real time, and solving problems that don’t have obvious answers. We’re looking for people who find that energizing rather than stressful.
• You’ll wear a lot of hats. One day you might be prospecting, the next helping refine positioning, jumping into onboarding calls, or working with product on customer feedback. If you prefer highly specialized roles with narrow ownership, this probably won’t be the right fit.
• We expect more than 9 to 5 — raw hours make an impact at our current stage. That said, we trust each team member to create a flexible work schedule that allows them to be most productive while accommodating other priorities outside of work. We also strongly encourage time off to recharge the batteries: in addition to unlimited PTO, we've implemented a minimum 20 days vacation policy