Manager, Commercial Expansion

About the role

You will own the expansion and growth of existing customers within the Commercial segment, focusing on the critical mid-market and small enterprise base under 750 employees. You will be the first sales leader to build out and establish our new Toronto sales hub, setting the foundation for a repeatable and scalable sales machine. This role demands a gritty, thoughtful, and curious leader who thrives on building processes from scratch. You will balance high-velocity sales motions with the occasional large strategic opportunity, ensuring consistent pipeline generation. Success in this position means becoming an expert in how Tailscale delivers security and connectivity value to our customers. You will lead by example, coaching your team and leveraging data to drive performance and exceed targets.

Key facts

What you'll do

Conduct in-depth discovery and qualification of expansion opportunities within existing customer accounts to identify and prioritize new use cases.

Develop and own a repeatable sales playbook for the Toronto expansion hub, including forecasting, pipeline management, and win-loss analysis.

Lead by example through active prospecting, conducting role plays, and unblocking critical opportunities for your team.

Establish best practices for customer relationship building and executive-level engagement strategies tailored to the Commercial segment.

Utilize sales data and performance metrics to coach account executives, refine territory plans, and drive continuous improvement.

Collaborate closely with sales engineering, product, marketing, and partnership teams to build compelling value propositions and accelerate complex deals.

Travel to industry events and customer locations once a quarter to build relationships, gather insights, and represent Tailscale at the highest level.

Own the end-to-end sales cycle for target accounts, from initial contact through negotiation, contract finalization, and expansion.

Partner with customer success to ensure smooth onboarding, adoption, and identification of further expansion opportunities.

Maintain a rigorous pipeline management process to ensure consistent achievement of quarterly and annual quotas.

Champion the Tailscale brand and its value proposition in every interaction, reinforcing trust and security.

Analyze competitive landscape dynamics and adjust sales strategies to maintain a decisive advantage in the market.

Drive the creation of localized content and messaging tailored to the Canadian Commercial market.

Act as a subject matter expert on Tailscale's product suite, translating technical capabilities into clear business outcomes for buyers.

Requirements

You must possess 1+ years of sales management experience in a B2B SaaS/Software company, demonstrating a proven track record.

You must exhibit an aptitude for delivering world-class customer experiences, operating with urgency and curiosity.

You must have excellent written and verbal communication skills to articulate value and negotiate effectively.

You must be capable of managing many activities and tasks simultaneously in a fast-paced environment.

You must be willing to travel to industry events once a quarter to maintain market presence and network.

This role is based in Toronto and requires a hybrid schedule of 3 days per week in-office.

You must be legally authorized to work in Canada without sponsorship.

You must have a strong understanding of SaaS sales motions and the technical selling of security products.

You must be comfortable working with data, quotas, and performance metrics to drive results.

You must have experience building and leading a sales team from the ground up.

You must be able to operate independently and make sound decisions with limited direct supervision.

You must have a history of exceeding sales quotas and achieving ambitious targets.

Nice to have

Experience selling to mid-market and enterprise customers in the technology sector.

Familiarity with network security, Zero Trust, or SASE concepts.

Prior experience building a sales function in a hybrid or fully distributed organization.

Practical notes

This is a full-time position based in Toronto, Ontario, requiring a hybrid schedule of 3 days per week in the office.

Travel expectations include attendance at industry events once a quarter.

Candidates must have legal authorization to work in Canada without the need for sponsorship.