GTM Specialist - Private Operators

OffstreetRegina, SK

About The Position

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.

Requirements

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

Nice To Haves

  • 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.

Responsibilities

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.

Benefits

  • Opportunity to make a measurable impact
  • Collaborate with a high-performing team
  • Help shape how we scale our go-to-market motion
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