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VP of Sales - Remote

Post Date

Dec 08, 2025

Location

Watertown,
Massachusetts

ZIP/Postal Code

02472
US
Feb 13, 2026 Insight Global

Job Type

Perm

Category

Sales

Req #

BOS-1a09775b-755f-4c12-b253-c9b0f793e2a0

Pay Rate

$180k - $200k (estimate)

Job Description

An employer is looking for a roll-up-your-sleeves VP of Sales to own and drive all new business revenue (~$10–12M annually). This is a strategic and execution-focused role reporting directly to the EVP of Revenue and will be responsible for optimizing the company's existing sales playbook, lead enterprise sales efforts, and ensure the efficiency and scalability of our sales organization.
Key Responsibilities
• Revenue Leadership: Own the entire new business number (~$10M) across enterprise and SMB/mid-market segments.
• Team Oversight:
○ Directly manage 5 Enterprise AEs (top performers driving 55–60% of revenue).
○ 1 Sales Manager for SMB/mid-market team
○ Oversee BDR/SDR function (~10 reps) through their manager.
• Strategy & Execution:
○ Optimize and enhance the existing sales playbook.
○ Drive go-to-market strategies for new product launches.
○ Collaborate closely with Marketing for pipeline generation.
• Operational Excellence:
○ Improve team efficiency and performance within budget constraints.
○ Explore AI-driven enhancements for BDR/SDR productivity.
• Cross-Functional Leadership: Partner with the executive team to align sales strategy with company growth objectives.
Compensation for this role is 170-200k per year annually plus bonus/commission (OTE ~300-350k). Compensation may vary based on several factors, including skills, experience, and education. Benefit packages for this role may include healthcare insurance offerings and paid leave as provided by applicable law.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Required Skills & Experience

-5+ years of SaaS sales experience within fintech space
-2+ years of experience in a strategic sales leadership position
-Strong understanding of financial markets and technology
-Experience optimizing the sales playbook
-Ability to inspire and create a collaborative, resilient sales organization

Nice to Have Skills & Experience

-Wealth Tech SaaS experience

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.