Senior Account Executive, New Business A Senior Account Executive at Tiller owns full-cycle sales of net-new business, from qualified opportunity through discovery, solution development, proposal creation, negotiation, and close. You will sell across multiple Tiller service lines based on our ideal client profile (ICP), qualification criteria, and the client problem we are best positioned to solve. You will work closely with the CEO and Tiller subject-matter experts to progress high-quality opportunities, then transition new clients to our Client Delivery team for ongoing delivery and account growth.

This is a senior individual-contributor role with the opportunity to help build a more repeatable and scalable sales function over time.

Responsibilities

- Own qualified net-new opportunities through discovery, solution development, proposal creation, negotiation, close, and handoff to our Client Delivery team.

- Sell across Tiller's service lines based on client need, ICP fit, qualification criteria, strategic value, and Tiller's ability to deliver successfully.

- Build trust with senior B2B SaaS buyers and lead discovery that uncovers the business problem, desired outcomes, buying process, budget, timeline, and risks.

- Partner with the CEO, strategists, and delivery leaders when deeper expertise is needed, while steadily increasing your ability to run opportunities independently.

- Maintain an accurate pipeline and forecast, disciplined CRM management, and consistent revenue pacing throughout the year.

- Protect Tiller's pricing, scope, and margin standards to ensure revenue sold drives real value for the agency.

- Create clear and detailed handoffs to Account Management and Project Management teams to support an effective and efficient handoff from Recent Business to Client Delivery.





- Contribute to the playbooks and systems that make sales easier to scale.

- Contribute to and help shape pipeline development efforts beyond inbound leads, including outbound, ABM, networking, industry events, partnerships, and other business development activities designed to create qualified opportunities within Tiller’s ICP.

Requirements

- Have a proven B2B agency sales track record, including achieving annual new-business targets and quotas.

- Have experience closing six-figure annual retainer or project-based engagements and navigating multi-stakeholder, consultative sales cycles.

- Have sold agency or professional-services or other complex solutions where discovery, business judgment, and credibility matter as much as product / service knowledge.

- Build rapport quickly and sell in a consultative, low-pressure way while confidently moving opportunities forward.

- Can learn and sell across multiple service lines, operate independently as a senior individual contributor, and know when to involve subject-matter experts.

- Bring commercial judgment, integrity, attention to detail, ownership, and coachability to the sales process.

Success Looks Like

- Achieve the initial ramp quota of $750,000 in net-new business from October 1, 2026 through March 31, 2027, following a primary onboarding month in September 2026.

- Achieve a normalized annual quota of $1.5M beginning April 1, 2027, with healthy pacing and sufficient pipeline throughout the year rather than dependence on a single quarter or a few late-stage deals.

- Consistently bring in well-qualified, strategically aligned clients while maintaining healthy pricing, scope, and project-margin standards.

- Build proficiency and independence across Tiller's service lines while maintaining accurate forecasts, disciplined CRM hygiene, reliable follow-through, clean handoffs, and a repeatable sales operating system.

📌 Senior Account Executive, New Business (Calgary)
🏢 Tiller Digital
📍 Calgary