Commercial Sales Executive- Financial Services

We are seeking a Client Executive who can drive value creation, retention, and expansion across mid-to-large enterprise accounts. In this role, you will own the growth strategy for your territory or vertical, developing long‑term customer relationships and ensuring consistent achievement of our services revenue objectives.

• Develop and execute growth strategies for medium and large enterprise accounts.
• Build deep understanding of client priorities and translate them into meaningful Windward opportunities.
• Strengthen executive relationships to drive retention, expansion, and long‑term partnership value.
• Lead account planning and territory strategy with disciplined pipeline and forecast management.
• Navigate complex buying cycles, negotiate agreements, and close services engagements.
• Coordinate internal teams—including Pre‑Sales, Delivery, and Executive leadership—to support customer needs and strategic pursuits.
• Stay current on competitive trends and market movements within the Service Now and enterprise services ecosystem.

• Expand Windward’s presence within strategic accounts by uncovering high‑value opportunities tied to enterprise transformation.
• Build and deepen executive relationships, positioning Windward as a trusted advisor across Service Now, ITSM, AIOps, CMDB, and reliability initiatives.
• Influence client direction through strategic insight, clear recommendations, and outcome‑based roadmaps.
• Strengthen retention and loyalty by ensuring delivery excellence and proactive executive engagement.
• Accelerate company growth by securing net‑new logos and driving significant annual consulting revenue.

• 7+ years of consultative sales experience in high‑technology services, ideally within the Service Now, ITSM/ITOM, or Enterprise Management space.
• Demonstrated success selling into mid‑to‑large enterprises with consistent C‑suite engagement.
• Strong executive presence and business acumen, with the ability to diagnose enterprise challenges and shape integrated solutions.
• Proven track record of $3M–$5M+ in annual consulting revenue through a mix of net‑new wins and account expansion.
• Expertise in managing complex, full‑lifecycle sales motions and building compelling, value‑driven business cases.
• Deep understanding of enterprise industry verticals relevant to the assigned territory.
• Skilled in delivering high‑impact presentations and leading executive‑level discussions.
• Proficiency with CRM and pipeline management tools (Salesforce preferred).
• High integrity, a strong work ethic, and a results‑oriented mindset.

• A strategic, consultative sales professional who builds strong, trust‑based relationships.
• Motivated, intellectually curious, and consistent in delivering on commitments.
• Confident engaging across all levels of an organization, from technical teams to the C‑suite.
• Passionate about technology, transformation, and driving meaningful client outcomes.
• A collaborative team member who exemplifies.

• Competitive base salary aligned with experience and performance expectations.
• Uncapped commission potential with significant earning upside.

Windward strives to attract and retain the best individuals and provide an environment where they can grow professionally and build a rewarding career. We offer Medical, Dental, Vision, Flexible Spending Accounts, Short Term Disability, Long Term Disability, Life Insurance and AD&D, the option to purchase additional Life Insurance and AD&D, Paid Time Off, Personal Leave, Holidays, 401(k) plan with company match, and work/life balance.

Windward is proud to be an Equal Opportunity Employer. Applicants are considered for all positions without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, ancestry, marital or veteran status.