Director of Sales – Customer Expansion (Account Management)

HubSync is seeking a Director of Sales to lead our Account Management organization, responsible for cross-sell, upsell, and expansion revenue across our customer base within the Top 400 CPA firms   

This leader will own expansion ARR, build pipeline discipline inside the install base, and elevate the team from reactive account coverage to proactive, value-driven revenue generation. 

This is not a customer support or renewal management role. This is a revenue leadership position responsible for driving measurable expansion within complex, multi-office CPA firms. 

What You Will Own 

Revenue & Pipeline 

• Annual expansion ARR target 

• 4x+ pipeline coverage within the install base 

• Forecast accuracy and deal execution rigor 

• Multi-product penetration across accounts 

Operating Cadence 

• Weekly pipeline inspection (not review — inspection) 

• Account plans for each customer accounts 

• Value hypotheses and quantified business cases 

• Executive engagement strategy inside top firms 

Strategic Account Growth 

• Expansion into new business units 

• Cross-sell of AI modules and new products 

• Multi-year expansion strategies 

• Executive-level relationship mapping (Managing Partner, CEO, CIO, COO, CTO) 

Responsibilities 

• Lead and coach a team of Account Managers responsible for expansion revenue 

• Execute a structured expansion playbook (segmentation, whitespace mapping, MAPs) 

• Partner closely with Customer Success on health scoring and timing of expansion 

• Implement disciplined opportunity management (MEDDPICC or similar) 

• Create expansion forecasting framework 

• Elevate team from order-takers to strategic advisors 

• Drive executive-level expansion conversations 

• Build expansion metrics dashboard (coverage, attach rate, product penetration) 

Ideal Candidate Profile 

Experience 

• 7+ years in SaaS sales 

• 3+ years leading expansion / customer sales teams 

• Sold and managed $100K–$1M+ ACV accounts 

• Experience with multi-product SaaS platforms 

• Exposure to CPA, financial services, compliance, or workflow automation strongly preferred 

Skills 

• Can build pipeline inside an existing customer base 

• Strong value-based selling discipline 

• Comfortable driving executive-level conversations 

• Data-driven and operationally rigorous 

• Builds process without killing momentum