Sales Director

About Us

Well-known financial advisors Michael Kitces and Alan Moore witnessed firsthand the growing demand for fee-for-service financial planning. This inspired them to create a solution that could streamline billing processes for advisors while ensuring regulatory compliance. Since its public launch in 2018, AdvicePay has become a cornerstone of the financial planning landscape, serving thousands of advisors and firms nationwide and earning recognition for its innovative approach.

Today, AdvicePay continues to grow and adapt with new features and partnerships, enhancing the platform's capabilities. Driven by our belief in the fee-for-service model, our mission remains clear: to empower advisors and firms in offering fee-for-service financial planning. Our aim is to make getting paid for advice easy and scalable for everyone involved – from advisors to the home office, and clients. As the industry evolves, we're dedicated to staying ahead of the curve, ensuring that AdvicePay remains the trusted solution for financial professionals nationwide.

We are headquartered in Bozeman, Montana and we are incredibly proud to be listed on the Inc. 5000 list of America's Fastest-Growing Private Companies for 3 years in a row, as well as being recognized as a 2022 WealthTech 100 company, which places us among the top 100 innovative FinTech providers in the world addressing opportunities faced by the wealth and asset management industries.

You’ll love working here if you value - and want to contribute to - a positive, inclusive, innovative, and “Get Sh*t Done” culture where teammates help one another succeed and are committed to doing the right thing. If you're up for the challenge of disrupting an industry, join us.

About the Position

The Sales Director plays a pivotal role in driving revenue growth across multiple SaaS product lines, currently AdvicePay and AdvisorBOB. This role blends strategic leadership with direct selling, ensuring the sales team consistently achieves and exceeds revenue goals.  

As a player-coach, you’ll oversee multi-product pipeline performance, mentor and develop Account Executives, and personally lead and close key Mid-Market and Enterprise deals. Reporting to the Head of Sales & Marketing, you’ll serve as the bridge between leadership and the front line, translating vision into execution and fostering alignment across sales teams. 

This is an exciting opportunity to join a fast-growing, mission-driven SaaS company driving innovation across two complementary product lines that are transforming how financial firms operate. If you’re passionate about building high-performing teams and love rolling up your sleeves to close deals, this is the role for you.

What You’ll Be Doing

Sales Leadership Across Product Lines

• Oversee day-to-day sales execution for multiple SaaS product lines (AdvicePay and AdvisorBOB). 

• Translate strategic objectives into actionable sales goals, plans, and daily activities for the team. 

• Maintain visibility into pipeline health, forecast accuracy, and team performance across product lines. 

• Partner closely with the Head of Sales & Marketing to ensure alignment between execution and strategic direction. 

• Design, implement, and oversee ongoing sales training programs focused on mastering our products and becoming stronger SaaS sales professionals. 

Player-Coach

• Personally lead and close select Mid-Market and Enterprise sales opportunities. 

• Negotiate high-complexity sales cycles (ex: RFPs, multi-stakeholder, legal/security review, etc.) to drive favorable outcomes.

• Stay up-to-date on financial services and the fintech landscape. Leverage market knowledge, competitive dynamics, and buyer behavior to inform positioning, guide prospects, and close deals.

• Represent both products at key conferences, leading booth engagement and networking opportunities.

Team Leadership - Lead, Manage, Hold Accountable (LMA)  

• Manage the full team member lifecycle for direct reports (Account Executives today): hiring, onboarding, performance management, coaching and correction, and career development.

• Lead, manage, and hold team members accountable to clear expectations, using EOS tools (L10 meetings, scorecards, quarterly conversations, etc.) to support clarity, alignment, and performance.

• Champion a culture of continuous learning, providing regular coaching, feedback, and development opportunities tailored to each team member's goals and strengths.

• Conduct regular 1:1s and quarterly conversations consistent with AP’s people processes and standards.

• Join key sales calls and offer real-time deal support to guide reps and accelerate opportunities. 

Sales Strategy & Deal Management 

• Guide team-level deal strategy and negotiation, stepping in on complex deals and escalating to Head of Sales & Marketing when necessary.

• Apply standard pricing guidelines and escalate non-standard requests to the Head of Sales & Marketing.

• Contribute to Account Executive quota planning, providing key insights to Head of Sales & Marketing regarding pipeline, market dynamics, and team capacity.

• Track negotiation trends and provide feedback to improve contracts and streamline redline cycles. 
  

Pipeline & Process Management 

• Own pipeline health, coverage, progression, and sales activity.

• Identify and recommend improvements to streamline sales cycles. 

• Ensure consistent adoption of sales process and CRM discipline (HubSpot).

• Share timely, accurate updates with the Head of Sales and Marketing to support planning and forecasting.

Cross-functional Collaboration 

• Act as a liaison between frontline sales and the Head of Sales & Marketing to ensure alignment on goals and execution.

• Gather and share prospect insights with Product and Marketing to influence the roadmap, product positioning, and marketing campaigns.

• Identify enablement needs to request tools, resources, or training to support rep success.

• Other duties as assigned.

The Deets

• Start Date: February 2026

• Status: Exempt, Full-time (40-45 hours/week)

• Location: Bozeman, MT

• Department: Sales and Marketing

• Reports to: Head of Sales and Marketing

• Direct reports: 3 Account Executives

• Travel: 10% (3-4 conferences per year to start)

Compensation & Benefits

• Salary: $201,571/year (please note this salary is inclusive of total earnings for this role. We do not have a commission or bonus structure at AdvicePay)

• Flexible paid time off days to maintain work-life harmony (we encourage and support that you take at least 3 weeks off per year!)

• 11 paid holidays when the office is closed

• 401(k) with match - you put in 6% and we put in 4.5%

• 12 weeks of paid parental leave for the birth or adoption of a child

• Health benefits package provided of up to $450/month for an individual, $1000/month for families

• Dental, Vision, Voluntary Life and AD&D, and Accident insurance options

• Employer-paid life insurance

• Employer-paid long-term disability coverage

• Up to $1800/year to cover the cost of working with a financial planner, plus up to $500 toward the one-time upfront fee

• $250/quarter to spend on yourself specific to our core value of “Be Well Being You”

• $500 donated to a non-profit organization of your choice when you volunteer 40 hours/year

• $2,000/year in Professional Development funds

• A sabbatical program that includes a cash bonus and extra time off at 5, 10, and 15 years

• Subsidized employer-sponsored childcare through our internal daycare program for Bozeman area Team Members

• Pet insurance

• Company-owned laptop provided

Please see our Team Member Handbook to learn more about the benefits and perks we offer!

What You’ll Bring to the Table (If you think, “I only meet 80% of these qualifications”, still apply!)

• 5+ years of B2B SaaS sales experience, with at least 2 years in a people management role.

• Proven success leading multi-product or multi-segment SaaS sales organizations, ideally across mid-market and enterprise tiers. 

• Demonstrated ability to personally close complex, multi-stakeholder deals with long sales cycles.

• Experience managing Account Executives with 1-5 years of experience and developing them into consistent quota achievers.

• Track record of scaling revenue and improving sales performance through process discipline, coaching, and data-driven decision making. 

• Strong understanding of pipeline management, sales forecasting, and driving consistent sales process adoption.

• Executive presence capable of engaging C-suite decision makers, influencing outcomes, and representing the company. 

• Comfortable using and enforcing CRM best practices (like HubSpot).

• Active use of structured sales methodology (MEDDPICC, Challenger, Sandler, etc.). 

• Ability to work cross-functionally with product, customer success, and marketing teams, especially in high-stakes deals.

• High sense of personal responsibility + integrity. (required)

• An understanding of and strong alignment with our core values. (required)

• Legally authorized to live and work in the United States. (required)

What Will Make You Stand Out From the Crowd

• Fintech or WealthTech experience. You understand the financial services industry, especially RIAs, broker-dealers, and the compliance complexities they face. 

• You’ve unified or led multiple product-line sales teams, balancing GTM, ICPs, and metrics without losing focus or accountability.

• You thrive on scaling processes, leading through growth, and shaping culture in fast-evolving teams. 

• Experience working within a structured operating system like EOS (Entrepreneurial Operating System). 

• Experience working in non-commission sales environments, with a proven ability to build motivation and performance culture without variable compensation.

Application

• In lieu of a cover letter, please respond to the following prompt in 2–3 paragraphs:
  Describe the most complex SaaS deal or sales initiative you’ve led. In your response, please reference the specific role(s) on your resume where you gained the experience you’re drawing from. How did you personally drive the outcome while leading your team, and what does this example reveal about your approach to sales leadership?

• Resume (to be uploaded)

Note on AI use: While AI is a useful tool for refining your work, please ensure this response is primarily in your own words and reflects specifics from your own experience. We're interested in seeing your unique communication style and personality shine through.

Applications will be reviewed as they are received. Please note that we review every application individually, and because our team is small, we’ll be closing this posting once we’ve received a manageable number of applicants (around 50 - 75). If you’re interested in this role, we encourage you to apply sooner rather than later - we don’t want you to miss the window!

Process

1. Initial phone screen answering a few short questions about AdvicePay and the position

2. First-round interview with the hiring manager

3. Work sample

4. Final round, including:

   • Company Core Values interview

   • An informal coffee chat to get to meet some current AP team members

   • Executive team member interview

   • Final wrap interview with the hiring manager

Our typical hiring process takes 4-6 weeks from when we first post the job to when we extend a final offer

After applying, please be on the lookout for an email from us confirming receipt of your application, as well as future correspondence (emails sometimes get caught in your Junk/Spam folder or a Promotions tab)

AdvicePay believes that our Team Members, and the individual identities and experiences of our Team Members, are our key differentiators. We won't settle for mere acceptance of each other's differences because we maintain that our Team is better because of our differences, not in spite of them. As such, our culture celebrates, champions, supports, protects, and thrives on our various and collective identity categories. AP is beyond proud to be an equal opportunity employer.