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Pennylane is a high-growth fintech company serving small businesses, with 900,000 customers as of January 2026 (3x growth in 2025). The Small Business Account Executive team converts self-signup leads into paying customers, currently managing 2,500 leads per month.
You will lead a pod of 5 Account Executives (AEs) in full-cycle sales targeting micro-businesses (0–5 employees). Your primary responsibility is to drive revenue (MRR) while building and developing a high-performing team. The broader AE Small Business team is scaling rapidly from 10 people with mostly junior closers, requiring structured management and coaching.
Key responsibilities:
**Team Management**
- Manage and develop 5 AEs, conducting weekly 1:1s, team rituals, pipeline reviews, and sync meetings
- Coach team members on methodology, lead qualification, and closing techniques
- Set individual and collective MRR targets; manage performance gaps with targeted coaching plans
- Foster team culture, well-being, and retention
**Performance & Analytics**
- Track KPIs: activity volume, MRR signed, conversion rates, deal velocity, lead processing speed
- Analyze pod performance via Salesforce and Metabase; identify improvement levers
- Escalate field insights and propose corrective actions
- Participate in sales calls alongside the team
**Process & Continuous Improvement**
- Contribute to refining outreach messaging and sales approach
- Test new tactics and share best practices across the team
- Ensure compliance with sales policy
- Collaborate with SDR, Marketing, Ops, and Data teams to optimize lead quality and conversion
- Serve as liaison between pod and cross-functional teams (Care, Onboarding, Ops)
- Gather and relay product and commercial feedback from the field
**Requirements**
- 3+ years of B2B or B2C closing experience, ideally in high-volume, short-cycle, full-cycle environments
- Proven track record of achieving and exceeding MRR/revenue targets
- 1+ year of team management or team lead/mentor experience (ideally 3–5 people); strong operational and mentoring experience can substitute for formal management tenure
- Proficiency with CRM tools (Salesforce), analytics platforms (Metabase), and KPI-driven management
- Preferred: background in accounting, fintech, or SaaS sectors
- Strong communication and active listening skills; ability to close quickly in low-touch contexts
- Natural leadership; ability to deliver direct, constructive feedback
- Analytical mindset; comfort managing multiple projects and 5 direct reports simultaneously
- Collaborative spirit; adaptability to fast-growing startup environment
- Results-oriented with ambition to exceed targets
- Pedagogical mindset; genuine desire to develop team members
- Proactive; comfortable proposing process and performance improvements
- Resilient; able to sustain high energy in a high-volume, high-pressure MRR environment
- Coachable; strong desire to grow as a manager
