Senior SDR, Player-Coach

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior SDR, Player-Coach in Canada.

This role blends high-performance outbound sales execution with emerging leadership influence in a fast-paced B2B SaaS environment. You will be responsible for driving pipeline generation through strategic, multi-channel prospecting while consistently meeting and exceeding quota expectations. Alongside your individual contributor responsibilities, you will act as a senior presence on the team—helping shape best practices, elevating peer performance, and contributing to the evolution of the outbound playbook. The environment is highly collaborative, growth-oriented, and focused on building scalable revenue systems. You will work closely with sales, marketing, and leadership teams to refine messaging, improve targeting, and strengthen overall pipeline quality. This is an opportunity for an experienced SDR who wants to remain in the field while stepping into broader influence and coaching impact.

You will be responsible for driving outbound pipeline generation while also contributing to team development, sales enablement, and continuous improvement of SDR practices across the organization.

• Own a personal outbound quota targeting L&D, HR, and People leaders across mid-market and enterprise accounts
• Execute multi-channel prospecting campaigns using email, LinkedIn, phone, and video outreach
• Partner closely with Account Executives to penetrate target accounts and build qualified pipeline
• Maintain and optimize activity and pipeline data within CRM and sales engagement tools
• Contribute to continuous improvement of outbound messaging, cadences, and targeting strategies
• Coach and support peers by sharing best practices across calls, emails, and account strategies
• Collaborate with marketing and sales leadership on campaign execution and playbook development
• Support onboarding and ramping of new SDR team members as the function scales
• Act as a role model for high-quality outbound execution and pipeline discipline

Requirements

The ideal candidate brings strong SDR experience in B2B SaaS, with a proven track record of quota attainment, strong communication skills, and the ability to influence and elevate peers while still excelling as an individual contributor.

• 3+ years of SDR or B2B outbound sales experience in a SaaS environment
• Consistent track record of exceeding outbound pipeline or meeting booking quotas
• Strong expertise in multi-channel prospecting and personalized outbound strategies
• Excellent written and verbal communication skills
• Strong understanding of sales funnels, pipeline metrics, and performance analysis
• Experience working with tools such as Salesforce, LinkedIn Sales Navigator, Gong, or similar platforms
• Natural coaching mindset with ability to support and elevate peers informally
• Strong organizational skills and ability to manage high-volume outbound activity
• Genuine desire to remain hands-on in selling while taking on leadership influence

Benefits

• Competitive compensation aligned with experience and performance
• Remote-first work environment with flexibility across Canada and North America
• Unlimited PTO policy
• Additional wellness and personal recharge days (including birthday off)
• Comprehensive health, dental, and vision coverage from day one
• Professional development opportunities and access to learning resources
• Supportive, collaborative culture with a focus on growth and continuous learning
• Opportunity to shape outbound strategy and influence team development without leaving an IC role