GTM Specialist - Private Operators
About Offstreet
Offstreet is helping parking operators modernize how they manage guest parking through simple, scalable technology. As we continue to grow, we’re looking for a proactive, resourceful GTM Specialist to help accelerate pipeline growth within the Private Operator market.

This is a high-impact role focused on outbound prospecting, campaign execution, and generating qualified opportunities for the GTM team. You’ll play a key role in building relationships, testing outreach strategies, and helping us scale our go-to-market efforts.

We’re looking for someone who’s curious, organized, driven, and excited to contribute directly to company growth.

What You’ll Do
Outbound Prospecting & Lead Generation

Own outbound prospecting efforts within the Private Operator market.

Build and refine target account lists using ICP and segmentation strategies.

Research prospects to personalize outreach and improve engagement rates.

Use email, LinkedIn, phone, and other outbound channels to generate conversations.

Book qualified meetings for the sales/GTM team.

Campaign Execution & Optimization

Execute outbound campaigns including webinar follow-up, ABM plays, and targeted outreach initiatives.

Draft and test messaging across email sequences, LinkedIn outreach, and call scripts.

Run A/B tests to improve open rates, response rates, and meeting conversions.

Track campaign performance and continuously optimize based on insights and results.

Sales Development Operations

Maintain clean and accurate records in HubSpot.

Monitor buyer intent signals and respond quickly to engagement opportunities.

Manage outreach sequences, cadences, and task queues using tools like HubSpot, Apollo, or similar platforms.

Follow up with inbound leads, form submissions, and event attendees.

Collaboration & Feedback





Collaborate closely with Sales and Marketing on campaigns, messaging, and outreach strategy.

Share learnings from the field including objections, trends, and persona insights.

Help improve lead handoff processes and pipeline visibility across the GTM team.

Participate in weekly GTM syncs and performance discussions.

Metrics & Performance

Own key KPIs including outreach activity, meetings booked, and opportunities created.

Report weekly on pipeline performance, learnings, and optimization opportunities.

Consistently contribute to revenue goals by driving top-of-funnel growth.

What Success Looks Like

A consistent pipeline of qualified outbound meetings.

Strong response and conversion rates driven by personalized outreach.

Clear ownership and execution of outbound prospecting motions.

A proactive team member who brings ideas, accountability, and results.

Who You Are

2+ years of experience in sales development, outbound prospecting, marketing or a GTM-focused role.

Robust written and verbal communication skills.

Organized, self-motivated, and comfortable working in a fast-paced startup environment.

Comfortable experimenting with messaging, tools, and outreach strategies.

Curious, resourceful, and motivated by results.

Bonus Points

Experience with HubSpot, or similar sales tools.

SaaS or B2B startup experience.

Familiarity with account-based marketing (ABM) or multi-channel outbound campaigns.

Experience selling into parking, operations, facilities, or related industries.

Why Join Offstreet?
We’re building technology that simplifies parking operations and creates better experiences for operators and their customers.

At Offstreet, you’ll have the opportunity to make a measurable impact, collaborate with a high-performing team, and help shape how we scale our go-to-market motion as we continue to grow.

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📌 GTM Specialist - Private Operators (Saskatchewan)
🏢 Offstreet
📍 Saskatchewan