Senior SDR, Player-Coach

Jobgether; Canada; Remote; CAD 80,000 - 120,000; Full time

Benefits offered by this job

Medical coverage

Unlimited PTO

You Days

Birthday PTO

Professional development

Remote-friendly

Leadership pathway

Enterprise exposure

Collaborative culture

SaaS growth

Job summary

Jobgether in Canada is seeking a Senior SDR, Player-Coach to lead outbound prospecting, own a personal pipeline, and mentor peers while remaining hands-on with sales execution.

You will collaborate with AEs, Marketing, and Revenue leadership to build scalable playbooks, optimize multi-channel outreach, and drive enterprise pipeline across L&D/HR segments.

Qualifications

• 3+ years as an SDR in B2B SaaS with outbound quotas.

Responsibilities

• Own an individual pipeline-generation quota focused on L&D, HR, and People leaders.
• Execute multi-channel outbound campaigns across email, LinkedIn, phone, and video with personalized outreach to senior decision-makers.
• Partner with Account Executives to identify target accounts, develop multi-threaded relationships, and generate qualified enterprise pipeline.
• Use CRM, conversation intelligence, prospecting, and enrichment tools to improve outbound performance.
• Serve as a benchmark for high-quality SDR execution and provide examples of messaging and account strategy.
• Coach peers on outbound cadences, calls, emails, account planning, and SDR enablement.
• Collaborate with Marketing, Sales Operations, and Account Executives to improve campaign execution, data quality, tooling, and pipeline quality.
• Share successful practices, identify performance gaps, and raise overall SDR effectiveness.
• Support interviewing, onboarding, and ramping of new SDRs as the team grows.
• Contribute to a high-performance culture through hands-on leadership and consistent sales execution.

Skills

Outbound sales

Coaching

Cross-functional collaboration

Data analysis

Multichannel outreach

Enterprise sales

Quota ownership

Remote collaboration

Tools

Salesforce

Gong

LinkedIn Sales Navigator

FullEnrich

Job description

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior SDR, Player-Coach based in Canada.

This is a senior individual contributor role designed for an experienced B2B SaaS SDR who wants to expand their influence without stepping away from sales execution. You will own a personal outbound pipeline and quota while becoming a trusted coaching resource for the wider SDR team. The role combines high-quality prospecting, enterprise account development, peer coaching, and sales playbook development. You will work closely with Account Executives, Marketing, Sales Operations, and revenue leadership to build pipeline that converts. Your expertise will help refine outbound strategies, improve team performance, and establish scalable sales practices. The environment is collaborative, fast-paced, remote-first, and focused on meaningful ownership and measurable results. For a high-performing SDR ready for greater responsibility and a path toward leadership, this role offers a strong next step without leaving the field.

Accountabilities:

• Own an individual pipeline-generation quota focused on L&D, HR, and People leaders across mid-market and enterprise organizations.
• Execute multi-channel outbound campaigns across email, LinkedIn, phone, and video, using thoughtful personalization to engage senior decision-makers.
• Partner with Account Executives to identify target accounts, develop multi-threaded relationships, and generate qualified enterprise pipeline.
• Use CRM, conversation intelligence, prospecting, and enrichment tools effectively while continuously identifying opportunities to improve outbound performance.
• Serve as a benchmark for high-quality SDR execution and provide examples of effective prospecting, messaging, qualification, and account strategy.
• Coach peers on outbound cadences, calls, emails, account planning, and other aspects of sales development.
• Collaborate with revenue leadership and Marketing to develop and continuously improve SDR playbooks, messaging, cadences, ICP definitions, qualification standards, and handoff processes.
• Partner with Marketing, Sales Operations, and Account Executives to improve campaign execution, data quality, tooling, and pipeline quality.
• Share successful practices, identify performance gaps, and help raise the overall effectiveness of the SDR team.
• Support the interviewing, onboarding, and ramping of new SDRs as the team grows.
• Contribute to a high-performance culture through hands-on leadership, knowledge sharing, and consistent sales execution.

Requirements:

• 3+ years of experience as an SDR in B2B SaaS, with a demonstrated history of consistently achieving or exceeding outbound quotas.
• Strong outbound sales skills, including experience with personalized email, cold calling, LinkedIn prospecting, and multi-channel sequencing.
• Genuine motivation to continue carrying an individual quota while taking on coaching and team-development responsibilities.
• Proven ability to coach peers, mentor colleagues, identify process gaps, and proactively contribute to improvements without requiring formal management authority.
• Strong written and verbal communication skills, with the ability to engage senior executives and create compelling, concise sales messaging.
• Strong data fluency, including the ability to analyze funnel performance, diagnose conversion issues, and distinguish activity challenges from messaging or targeting problems.
• Experience selling to L&D, HR, or People leaders is strongly preferred, particularly within L&D, HR technology, EdTech, or Talent-related organizations.
• Enterprise sales development experience, particularly with organizations of 5,000+ employees, is highly valued.
• Previous informal leadership experience, such as peer training, onboarding ownership, mentoring, pod leadership, or SDR enablement.
• Familiarity with Salesforce, Gong, LinkedIn Sales Navigator, FullEnrich, and modern outbound prospecting and enrichment tools.
• Experience helping build an SDR function or working as an early SDR at a startup is a plus.
• Ability to work independently, remain accountable to measurable goals, and thrive in a fast-paced, high-accountability environment.
• Canada-based candidates are preferred, with Toronto-based professionals especially encouraged to apply; strong remote candidates elsewhere in North America may also be considered.

Benefits:

• Medical, dental, vision, and extended health coverage from day one.
• Unlimited paid time off.
• Company-wide "You Days" for rest and personal wellbeing.
• Paid time off on your birthday.
• Professional development opportunities, including access to internal mentors and extensive learning resources.
• Flexible, remote-first working model.
• Opportunity to grow from a senior individual contributor into a formal leadership position over time.
• Exposure to enterprise sales, category creation, and cross-functional revenue strategy.
• A collaborative, direct, inclusive environment that values high performance while supporting sustainable work practices.
• Opportunity to contribute to a growing SaaS business and help shape scalable sales processes and playbooks.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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