GTM Specialist

Build the best experience for universities. Own meaningful outcomes. Bring good vibes with high standards.

Offstreet is rapidly expanding in the Higher Education market, and we’re looking for a driven, relationship-focused GTM Specialist who can take a well-qualified pipeline and turn campus interest into long-term partnerships.

This role is not about cold calling or heavy prospecting. The top of our funnel is already strong.

This role is about:

• Running excellent demos
• Guiding campuses through multi-stakeholder conversations
• Navigating procurement
• Building strong relationships
• Closing deals

If you love helping people understand solutions, excel at keeping deals moving, and naturally take ownership of outcomes, this role will feel like home.

What You’ll Do

• Lead engaging discovery calls and deliver polished, value-focused demos.
• Develop a deep understanding of each campus’s structure, workflows, and challenges so every interaction is clear, professional, and genuinely helpful.

• Manage opportunities from the initial meeting through to closed-won, including leading discovery calls and demos, crafting proposals, and developing value-driven resources that support campus stakeholders throughout the decision-making process.
• Navigate Higher Ed procurement, approvals, and multi-department buying groups.
• Prepare proposals, pricing, and supporting materials that are accurate, compelling, and easy to understand.
• Maintain crisp pipeline management with forecasting within HubSpot.

• Prioritize building strong relationships across key campus stakeholders - Parking & Transportation, IT, Finance, Procurement, and Campus Safety - while proactively engaging additional influencers and decision-makers (multi-threading) to strengthen alignment and momentum.
• Show up with positivity, preparation, and respect in every conversation.
• Travel to conferences, campus meetings, and industry events when needed to support key opportunities.
• Collaborate closely with the full GTM team - including Sales leadership, Marketing, and Pipeline Operations - to ensure alignment on goals, share insights, and strengthen the feedback loop that drives continuous improvement across campaigns, messaging, and deal movement.
• Partner with Customer Success to ensure smooth, aligned handoffs post-sale.
• Share campus insights with Product and GTM teams to help shape messaging, process, and product decisions.
• Bring ideas, feedback, and solutions forward proactively.

What Success Looks Like

• Consistently moving opportunities from demo → proposal → close.
• Strong, trust-based relationships with campus stakeholders.
• Predictable, clear forecasting and deal updates.
• Fewer stalled deals, stronger conversion rates, and delighted campus contacts.
• A reputation on the team as someone who delivers results and lifts the people around them.

Who You Are

• 1–3 years in a customer-facing or problem-solving role, demonstrating strong communication skills, curiosity, and the ability to guide people through complex decisions.
• Confident communicator who enjoys leading demos and guiding conversations.
• Exceptionally organized with strong follow-through and clarity in communication.
• Relationship-driven, but also competitive and motivated by goals.
• Comfortable traveling for key meetings, conferences, and campus visits, which can average monthly and sometimes more depending on opportunities.
• Energized by working in a fast-moving, collaborative startup environment.
• Aligned deeply with Offstreet’s values:
  • Build the Best Experience - You care about delivering clarity, quality, and value.
  • Own the Outcome - You move deals forward and take initiative without waiting to be asked.
  • Good Vibes, High Standards - You bring positivity while holding yourself to a high bar.

Note: At this time, we’re prioritizing applications from local candidates (Regina/Saskatchewan-based).