Director, Sales

Fin • Chicago, IL

19d • $372,600 - $445,050 • Hybrid

About The Position

The Director, Sales will lead Fin’s North America New Business organization, overseeing Account Executives and their front-line managers who are responsible for new-logo and new-revenue growth across SMB and Mid-Market segments. Reporting to the VP, NAMER Sales, this leader owns the regional new-business strategy, operating plan, and results, and is accountable for building and running a high-performing, multi-layered sales organization.

The role requires an experienced second-line sales leader who can hire and develop sales managers, inspire a large team, and partner across functions to create efficient, repeatable, customer-centric sales processes. The Director will shape and execute a value-led sales strategy and scale the North America new-business engine in the AI-first customer-support market.

The position follows Fin’s hybrid working policy, with employees expected to work in the office at least three days per week. The OTE salary range for candidates within the Greater Chicago Area is $372,600–$445,050. Actual base pay depends on factors including education, skills, experience, and location. Regular employees may also be eligible for a corporate bonus or sales incentive, with the target included in OTE, and Restricted Stock Units (RSUs).

Requirements

• At least 5 years in a quota-carrying new-business individual-contributor role, with demonstrated success.
• Direct experience running strategic six- and seven-figure deals involving procurement, legal, security, and executive selling.
• At least 5 years of sales management experience.
• Track record of building and scaling new-business organizations across multiple segments, combining velocity and strategic selling in SMB and/or Mid-Market.
• Demonstrated success developing and executing outbound sales strategies.
• Strong new-business sales acumen.
• Strong command of forecasting principles and a track record of accurate regional revenue forecasting.
• Experience developing go-to-market strategy and building and executing operational plans covering capacity, territory, quota, and headcount.
• Excellent written, verbal, presentation, and interpersonal communication skills, including executive-level communication.
• Proof of eligibility to work in the United States is required.

Nice To Haves

• Experience in a product-overlay or co-prime selling environment.
• Experience with Command of the Message and MEDDPICC.

Responsibilities

• Partner with the VP, NAMER Sales and senior leadership to define North America new-business strategy across SMB and Mid-Market.
• Own segment planning, including territory and capacity design, headcount plans, quota setting, and resource allocation.
• Translate company goals into regional operating plans and tactics that reflect market dynamics and Fin’s opportunity.
• Hire, coach, and develop front-line Sales Managers, improving how they recruit, ramp, and manage Account Executives.
• Build a strong leadership bench and foster accountability, rigor, and continuous improvement.
• Own the regional new-business forecast and drive forecast accuracy and pipeline discipline across teams.
• Inspect pipeline health, deal progression, and conversion; intervene on strategic deals when needed.
• Analyze sales metrics to identify trends, optimize processes, and improve productivity and win rates.
• Partner with Marketing, SDR, Product, Sales Engineering, Enablement, RevOps, and Customer Success on go-to-market strategy, pipeline generation, and customer experience.
• Represent NAMER New Business in company planning and align goals, budgets, and investments.
• Maintain a deep understanding of customer needs, the competitive landscape, and market trends.
• Ensure thoughtful customer handoffs to the Relationship Management team while keeping customer experience central.

Benefits

• Benefits and resources intended to support health and wellbeing, family, time away from work, and financial future.
• Possible eligibility for a corporate bonus program or sales incentive; the sales incentive target is included in OTE.
• Possible eligibility for stock in the form of Restricted Stock Units (RSUs).

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed