Jobs in Regina, Canada

Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable.

We are seeking a Sales Manager to lead and scale a high-performing team of Account Executives (AE IIs) within our Advisors vertical. This leader will be responsible for driving revenue growth, building scalable processes, and developing top-performing sales talent.

This role begins with a structured onboarding immersion period (first 60–90 days) where you will engage directly in the sales cycle to deeply understand our business, advisors segment, and tools. This is not a "player/coach" role — the immersion period is designed to accelerate your impact as a leader.

You are a seasoned SaaS sales leader who thrives in high-growth, high-velocity environments — the kind where 50% of deals close within 7 days and efficiency, speed, and process are everything. You balance strategic thinking with hands-on execution, and you know how to build, scale, and inspire sales teams that consistently exceed expectations.

You bring a proven track record of leading quota-carrying teams in tech or SaaS, with the ability to coach both the "how" (process, pipeline, playbooks) and the "why" (vision, customer impact). You excel at developing talent, fostering accountability, and creating a culture of performance.

Most importantly, you understand how to scale a high-velocity sales motion while also moving upmarket. You've helped teams adapt to more complex, longer-cycle deals without losing the rigor of fast-paced selling. You're excited to lead a team that excels at speed today while preparing it for larger, more strategic opportunities tomorrow.

Onboarding Immersion (First 2–3 Months):

• Carry a limited personal quota to learn our sales cycle, advisor relationships, and product.
• Shadow and collaborate with AEs and Partnerships to gain fluency in our model.
• Surface early opportunities to improve workflows, pitches, and systems.

Leadership & Management (Post-Onboarding):

• Lead, mentor, and inspire a team of 5–8 AE IIs to consistently exceed pipeline and revenue goals.
• Scale and optimize a high-velocity sales motion (50% of deals closing within 7 days).
• Prepare the team for upmarket expansion, coaching them on navigating more complex, longer-cycle deals with larger advisors and institutions.
• Set clear performance expectations, track KPIs, and create a culture of accountability and excellence.
• Partner with Marketing, Partnerships, and Operations to optimize lead flow, pipeline quality, and conversion.
• Drive adoption and iteration of sales playbooks, outreach strategies, and CRM best practices.
• Hire, train, and onboard new sales talent to support rapid growth.
• Represent the sales team in cross-functional collaboration with Product, Legal, and senior leadership.

• 7+ years of SaaS sales experience, with at least 3+ years in direct sales management.
• Proven track record of leading high-velocity sales teams to exceed revenue targets.
• Experience working in a tech or SaaS company is required; fintech or advisor-facing SaaS strongly preferred.
• Skilled in developing talent, coaching future leaders, and building scalable processes.
• Strong executive presence and ability to influence cross-functionally.
• Proficient in CRM tools (HubSpot experience a plus).
• This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), Pennsylvania (PA), Texas (TX), Vermont (VT)

• Experience in fintech or estate planning SaaS.
• Background in financial advisor or wealth management partnerships.
• Experience scaling teams during high-growth or startup phases.
• A passion for helping families plan their legacy.

• Compensation: Salary + Equity
• Our OTE range for this position is $175,000 - $220,000, in addition to compensation we also include an employee equity package as a component of our offer along with other benefits and perks outlined below.
• PTO
• Flexible time off that you are encouraged to use
• Generous paid company holidays and breaks throughout the year
• Monthly friends & family day
• Paid time off to volunteer in your community
• Health and Wellness Benefits
• Fantastic health benefits including medical, dental, vision, life insurance, and generous parental leave
• Financial wellness benefits (Equity & tax advisory support, financial coach support, and employer-sponsored 401k with an employer match)
• Guest speakers & reimbursement for learning opportunities
• Extra
• Flexible work schedule + hours
• Family-friendly work environment. We support the complexity of a remote world with the needs of families
• Optional company-sponsored events and travel throughout the year
• $500 Work from home stipend + Apple accessories

• We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required.
• We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.
• Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.
• California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion (subject to exceptions). To exercise these rights, contact legal@trustandwill.com. For more information, visit our privacy policy.