Senior Sales Enablement Specialist

Newfoundland Time – Eastern Time | Canada

Application Deadline: Jan 16, 2025

Position Start Date: Feb 16, 2026

Compensation: Up to $120K CAD/year + OTE (based on sales OKRs)

About HeyOrca

HeyOrca is a fully remote company that values meaningful work and meaningful relationships. Our mission is to make marketing human by helping organizations build authentic communities.

We believe great software and great customer experiences are built by people who care deeply about their craft, their teammates, and their customers. At HeyOrca, Sales is a team sport. We focus on high-quality execution, strong systems, and constant learning so we can grow in a way that feels good for everyone.

The Role

We are seeking a Senior Sales Enablement Specialist who thrives in an early-stage, fast-moving environment and is excited by the opportunity to shape how selling happens across the team.

This is a senior individual contributor role focused on sales execution and system ownership. We are looking for someone that has been in the trenches of selling, but loves building the systems, processes, and operationalizing how to sell effectively and at scale.  

You will not carry a personal sales quota or territory. Instead, you will own the design and execution of programs that help the sales team build a strong pipeline and close better deals.

Your impact comes from defining outbound motions, setting the standard for deal quality, and scaling the systems and processes the sales team uses to win.

You are a seller by craft. You have personally sold in B2B environments, understand what it takes to create and close quality opportunities, and have strong instincts around discovery, value, and deal execution.

You also have real, hands-on outbound experience — not just designing programs, but doing the work yourself. You have built outbound engines by identifying target accounts, writing and testing messaging, running sequences, booking meetings, and learning from what actually converted.

At this stage in your career, you want to apply your sales experience by owning how selling happens across the team rather than managing salespeople or forecasting revenue.

Key Responsibilities

As a Senior Sales Enablement individual contributor, you will:

Build and own sales programs

• Design, execute, and continuously improve the programs, systems, and processes that power our sales motion
• Turn messy, early-stage sales work into clear playbooks and repeatable motions
• Create frameworks, templates, and training that help the team sell with confidence
• Partner closely with Marketing to align targeting, positioning, and outreach
• Build a self-sufficient sales motion so the team can generate pipeline consistently
• Measure program effectiveness and iterate based on real results
  

Own the outbound engine

• Define ICP segmentation, account targeting, and messaging frameworks
• Identify target accounts and personas
• Test and refine sequences and outreach through hands-on outbound work
• Set the standard for what good outbound looks like at HeyOrca
• Keep the outbound playbook current and practical
• Ensure learning loops exist from outreach to closed deals
  

Coach and mentor the team

• Coach reps on outbound execution, discovery, demos, and objection handling
• Review live outreach, calls, and demos to give direct feedback
• Help reps prepare for important demos and closing conversations
• Raise the baseline quality of execution across the sales team
• Provide sales coaching on objections, negotiation, and pricing discipline
  

Validate quality through hands-on work

• Run outbound alongside the team in controlled, limited ways
• Pressure-test new messaging and plays before rolling them out
• Review stalled or complex deals and recommend next steps
• Step in selectively to unblock progress when leverage is highest
• Ensure playbooks reflect what actually works in practice
  

Support demos and deal execution

• Run demos as needed, especially for complex or high-impact opportunities
• Help shape demo narratives and structure
• Support objection handling and pricing conversations
• Recommend ways to move deals forward
• Help unblock stalled deals
  
  

Qualifications

You bring:

• 5+ years of professional B2B sales experience
• Confidence in your personal ability to sell and close quality deals
• Strong hands-on outbound experience including prospecting, messaging, follow-ups, qualification, and demo booking
• Experience building and operating outbound motions yourself
• Clear standards around deal hygiene and execution quality
• A collaborative mindset with a bias toward execution
• Comfort operating in a fully remote environment
• Experience partnering with Sales and Marketing as the business moves upmarket
  
  

Nice to Have

• Experience working with HubSpot or similar CRMs
• Experience with AI-assisted tools for outbound messaging and learning loops
• Background in SaaS upmarket selling or Land and Expand motions
  

What This Role Is Not

This position is not focused on:

• Carrying a personal sales quota or territory
• Owning a revenue target or forecast
• Managing a team of sales reps
• Working primarily in RevOps or CRM administration
  
  

How We’ll Measure Your Impact

Success in this role looks like:

• A functioning, adopted outbound engine
• A clear and current outbound playbook used consistently by the sales team
• Pipeline self-sufficiency driven by outbound efforts
• Demo calendars consistently filled through sales-generated pipeline
• Improving quality and conversion of outbound-generated demos
• Rising outbound execution quality across the team
• Stronger discovery, better demos, and higher-quality wins
• Steady progress against Sales OKRs
• A Land and Expand program that supports expansion revenue
• Increasing Average Sales Price over time

Important Notes

• Salary includes OTE based on Sales OKRs, not personal quotas
• This role supports a 5-day company trip only. If you choose to extend your stay beyond the planned retreat dates, any additional travel costs must be covered by you
  

Perks include:

• 3 weeks vacation
• 2 weeks Christmas holiday
• Day off on your birthday
• $500 home-office allowance
• $500 yearly Orca wellness plan
• 5% RRSP matching
• $500/year personal development allowance

At HeyOrca, we are committed to building a diverse and inclusive workplace where every team member feels valued and empowered. We believe that our differences make us stronger and drive innovation. We welcome applications from people of all backgrounds, experiences, and perspectives. HeyOrca is an equal opportunity employer, and we do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Please note that we will only communicate with our job applicants by using @heyorca.com domains and no-reply@collage.co email. We will never contact applicants from any other email address. We will never ask for money or private information like SIN from potential employees. Be cautious of any unauthorized solicitations. You may view the most current and accurate job postings at HeyOrca by visiting https://www.heyorca.com/careers.