Sales Manager & Trainer

Job Description

Business Overview:

TimePayment is a leading FinTech company providing flexible equipment microfinancing solutions to small and mid-sized businesses across more than 30 industries. Our advanced technology platform and strong capital resources enable over 9,000 vendors and broker partners to deliver fast, streamlined financing options that support their customers’ growth. TimePayment has recently started a new chapter focused on growth, product innovation and technology transformation over the next 12 months. We are committed to offering the best digital experience, competitive programs, and high-quality service that helps our partners expand their sales and better serve their markets. If you are passionate about supporting business owners and contributing to a collaborative, high-performance organization, this role offers an opportunity to make a meaningful impact.

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Position Summary

The Sales Manager & Trainer partners closely with the Chief Revenue Officer (CRO) to lead day-to-day management, coaching, and development of the Vertical Account Executive Team. This role blends people leadership with hands-on sales enablement — using TimePayment's existing training framework to onboard, coach, and continuously develop Account Executives — while tracking performance against revenue and productivity targets to drive measurable growth across vertical markets.

·         Customer Centricity

·         Innovation & Technology

·         Team & Collaboration

·         Empowering Small Businesses

Key Responsibilities

Team Leadership & Management

• Partner with the CRO to manage day-to-day operations of the Vertical Account Executive Team, ensuring alignment with company revenue goals and sales strategy.

• Serve as a first-line resource for Vertical AEs — providing guidance, removing obstacles, and escalating issues to the CRO as needed.

• Support recruiting, onboarding, and ramp planning for new Vertical Account Executives.

Coaching, Mentoring & Training

• Deliver ongoing sales training using TimePayment's established training framework, adapting content and cadence to individual reps and vertical segments.

• Provide 1:1 coaching and mentoring on sales technique, product knowledge, objection handling, and pipeline management.

• Conduct call reviews, deal reviews, and shadow sessions to reinforce best practices and identify coaching opportunities.

• Onboard new hires against the existing training curriculum and track ramp-to-productivity milestones.

Performance Measurement

• Establish and monitor key performance indicators (KPIs) for the Vertical AE Team — activity levels, pipeline conversion, quota attainment, and deal velocity.

• Build and maintain regular performance reporting for the CRO, identifying trends, gaps, and coaching priorities.

• Support formal performance check-ins and review processes in partnership with the CRO and HR.

Business Growth

• Partner with the CRO to identify opportunities to grow vertical market share and expand account penetration.

• Collaborate cross-functionally with Marketing, Credit, and Operations to remove friction from the sales process and support growth initiatives.

• Contribute to sales strategy, territory/vertical planning, and goal-setting for the team.

Qualifications

• [Bachelor’s degree preferred, or equivalent combination of education and experience — confirm requirement].

• [X]+ years of experience in sales, sales management, or sales training — experience in equipment leasing/finance, micro-ticket or small-ticket finance, or related B2B financial services strongly preferred.

• Demonstrated track record coaching and developing a sales team to measurable performance improvement.

• Strong command of sales metrics, with the ability to translate performance data into specific coaching actions.

• Excellent presentation, facilitation, and interpersonal communication skills.

• Proficiency with CRM and sales performance/reporting tools [name specific systems, e.g., Salesforce].

• Ability to travel [insert expected %] to support field coaching and team meetings.

Required

• Coaching & Talent Development — builds capability in others through structured, ongoing feedback.

• Sales Acumen — credible with reps on technique, objection handling, and deal strategy.

• Data-Driven — uses performance metrics to prioritize coaching and resource allocation.

• Collaboration — works effectively across Sales, Credit, Operations, and Marketing.

• Adaptability — tailors coaching approach to different verticals, experience levels, and learning styles.