Who you are

You love connecting with business owners, asking thoughtful questions, and helping them see what is possible when they have the right financial information.

You know that great sales start with listening. You uncover the real challenges behind a prospect’s questions, build trust quickly, and explain how the right solution can help their business move forward.

You are just as comfortable starting a conversation with a new prospect as you are guiding an inbound lead from discovery to a signed agreement. You follow up consistently, handle objections confidently, and take ownership of your results.

You are organized, self-directed, and able to make a meaningful impact within a fractional schedule. Your CRM is current, your commitments are clear, and opportunities keep moving because you make them move.

You get fired up by the idea of crushing it and helping entrepreneurs turn accounting from a source of pain into a source of power.

Who we are

We believe entrepreneurs can change the world. Our role is to help them see through their financial blind spots with intuitive financial information that supports better decisions.

At Shift Financial Insights, we have developed a system that empowers entrepreneurs and changes how accounting is managed and delivered. Automated, systemized, simple. We are changing accounting for the better.

Our promise to customers In less than 15 minutes per month, our clients will:

· Clearly understand their financial position.

· Understand the top three to five financial issues facing their business.

· Have a plan of action to address those issues.

· Understand the non-issues they do not need to worry about.

We make financial information understandable and actionable, without requiring business owners to interpret a set of financial statements themselves.

What we do

We provide outsourced accounting departments for service-based businesses with $1 million to $18 million in revenue. Alongside day-to-day bookkeeping and controllership, we deliver data visualization, financial analytics and insights, and clear priorities that help entrepreneurs take action.

The purpose of your role

Own the full sales cycle on a fractional basis: generate outbound opportunities,



respond to and close inbound leads, and build an active referral partner network. Your goal is predictable, qualified revenue growth through clients who fit Shift’s services and operating model.

What we offer

- A remote, fractional opportunity with flexibility to organize your work around agreed commitments, client availability, and sales targets.
- The opportunity to own the sales cycle and make a measurable impact on Shift’s growth.
- Close collaboration with Operations, and Onboarding to deliver a strong experience from first conversation to client handoff.
- A team driven by clear expectations, accountability, and a shared commitment to helping entrepreneurs succeed.

Expected hours: 20 Hours per week

Compensation: TBD

Engagement type: Contractor with the potential to turn into Full Time

What the roles and responsibilities are

Outbound prospecting and referral partners

- Build a consistent pipeline through targeted calls, email, and LinkedIn outreach to Shift’s ideal clients.
- Identify, recruit, and support referral partners so they understand who Shift helps and can introduce qualified prospects.
- Maintain a consistent outreach and follow-up rhythm that fits your fractional schedule.

Inbound lead management and qualification

- Respond to every inbound lead within the same business day.
- Qualify prospects against Shift’s ideal client profile, including needs, fit, and readiness to move forward.
- Keep leads moving through the funnel with clear next steps and timely follow-up.

Discovery, solution selling, and demos

- Conduct introductory “first date” calls and deeper discovery conversations to understand business challenges, goals, and financial pain points.
- Present tailored service packages that connect Shift’s capabilities to the outcomes each prospect needs.




- Lead or coordinate technical demonstrations with the appropriate team members.

Proposal development and close

- Prepare and present accurate proposals that clearly outline pricing, scope, deliverables, and expectations.
- Handle objections, negotiate within agreed parameters, and guide qualified prospects to a signed agreement.
- Partner with Operations and Onboarding to confirm service fit and provide a complete handoff, including commitments made during the sales process.

Pipeline management and CRM discipline

- Keep Salesforce records, deal stages, notes, next steps, and tasks accurate and current.
- Provide weekly pipeline reporting and realistic sales forecasts.
- Identify stalled opportunities and deal risks early, and take action to move them forward.
- Participate in the weekly Sales & Marketing Level 10 meeting and deliver assigned quarterly priorities, known as Rocks.

What you bring

- Five or more years of B2B consultative sales experience selling to business owners.
- Experience owning the full sales cycle, from outbound prospecting and qualification through proposals, negotiation, and closing.
- Strong discovery and questioning skills, with the ability to build trust and connect solutions to business outcomes.
- The initiative, persistence, time management, and prioritization to deliver results with minimal oversight in a fractional role.
- Accurate, detail-oriented Salesforce documentation and disciplined follow-up.
- A cooperative approach to working with Marketing, Operations, and Onboarding to improve lead quality and client handoffs.

Interested in joining Shift?

Send your resume to [email protected] or apply directly through our website. Tell us about your experience owning a full sales cycle and delivering results in a fractional capacity.

We take finding the right person for the right seat seriously. Our selection process is designed to understand your skills, approach, and alignment with our core values.

We welcome applications from all backgrounds, experiences, and perspectives. We are committed to a supportive and collaborative environment where every team member feels valued and can thrive.

📌 Fractional Sales Associate (Canada)
🏢 Shift Financial Insights
📍 Canada