RVP, Enterprise Sales (Central)

Freshworks; Chicago (IL); Remote; USD 204,000 - 236,000; Full time

Job summary

Freshworks seeks an Enterprise Sales Leader in Chicago, responsible for leading a team of Account Executives. This role involves managing complex sales cycles while focusing on enterprise-level accounts. Ideal candidates will have extensive experience in SaaS sales capabilities and a proven ability to coach teams for high performance.

Benefits

Flexible PTO

Medical and dental insurance

Equity + ESPP

Wellness benefits

Parental leave benefits

Qualifications

• Must have a track record of success in managing enterprise sellers.
• Experience selling ITSM, CX, CRM, or EX solutions.
• Ability to coach through complex, high-value deals.

Responsibilities

• Lead and execute enterprise sales strategy in the Central U.S.
• Teach and coach the MEDDIC sales methodology.
• Oversee high-value, multi-threaded sales opportunities.

Skills

Sales Leadership

Enterprise Selling

Coaching

MEDDIC Knowledge

Quantitative Analysis

Education

10+ years in SaaS or enterprise technology sales

Tools

Salesforce

Modern Sales Tech Stacks

Job description

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Organizations everywhere struggle under the crushing costs and complexities of “solutions” that promise to simplify their lives. To create a better experience for their customers and employees. To help them grow. Software is a choice that can make or break a business. Create better or worse experiences. Propel or throttle growth. Business software has become a blocker instead of ways to get work done.

There’s another option. Freshworks. With a fresh vision for how the world works.

At Freshworks, we build uncomplicated service software that delivers exceptional customer and employee experiences. Our enterprise-grade solutions are powerful, yet easy to use, and quick to deliver results. Our people-first approach to AI eliminates friction, making employees more effective and organizations more productive. Over 72,000 companies, including Bridgestone, New Balance, Nucor, S&P Global, and Sony Music, trust Freshworks’ customer experience (CX) and employee experience (EX) software to fuel customer loyalty and service efficiency. And, over 4,500 Freshworks employees make this possible, all around the world.

Fresh vision. Real impact. Come build it with us.

Organizations everywhere struggle under the crushing costs and complexities of “solutions” that promise to simplify their lives. To create a better experience for their customers and employees. To help them grow. Software is a choice that can make or break a business. Create better or worse experiences. Propel or throttle growth. Business software has become a blocker instead of ways to get work done.

There’s another option. Freshworks. With a fresh vision for how the world works.

At Freshworks, we build uncomplicated service software that delivers exceptional customer and employee experiences. Our enterprise-grade solutions are powerful, yet easy to use, and quick to deliver results. Our people-first approach to AI eliminates friction, making employees more effective and organizations more productive. Over 72,000 companies, including Bridgestone, New Balance, Nucor, S&P Global, and Sony Music, trust Freshworks’ customer experience (CX) and employee experience (EX) software to fuel customer loyalty and service efficiency. And, over 4,500 Freshworks employees make this possible, all around the world.

Fresh vision. Real impact. Come build it with us.

Job Description

Freshworks (Nasdaq: FRSH) is seeking a high-impact Enterprise Sales Leader to coach and lead a team of Account Executives covering strategic accounts across the Central U.S. This front-line leadership role is critical to driving Freshworks’ continued growth in the enterprise segment. Reporting to the VP, NA Enterprise Sales, you will lead a team responsible for executing complex, multi-stakeholder sales cycles, leveraging the MEDDIC sales methodology to drive consistent revenue performance and long-term customer value.

This is an ideal opportunity for a multiplier; someone who can build teams and develop people.

Key Responsibilities

Regional & Strategic Execution:

• Own and execute Freshworks’ enterprise sales strategy in the Central U.S., with accountability for new business acquisition and expansion within accounts of 1,000+ employees.
• Support and refine territory planning and account segmentation across key verticals in your region.
• Align regional sales execution with broader go-to-market priorities, ensuring consistent messaging and field alignment.

Sales Methodology & Deal Leadership:

• Teach and coach MEDDIC (Metrics, Economic buyer, Decision criteria, Decision process, Identify pain, and Champion) to improve forecast accuracy, deal qualification, and pipeline health.
• Oversee high-value, multi-threaded sales opportunities from early-stage qualification to close, guiding reps in articulating differentiated value to C-level stakeholders.
• Engage directly in key strategic deals, partnering with solution engineers and executive sponsors to move opportunities forward.

Operational Discipline:

• Maintain rigor around pipeline reviews, forecast calls, and sales performance management, ensuring clear visibility into team health and revenue trajectory. This requires a strong quantitative presence and perspective.
• Leverage data to monitor performance and identify coaching opportunities.
• Drive continuous improvement in sales efficiency, customer acquisition cost (CAC), and sales cycle velocity.

Team Development & Culture:

• Recruit, onboard, and develop top-performing enterprise AEs with a focus on building a high-caliber team in the Central region.
• Foster a culture of accountability, excellence, and growth by delivering consistent coaching, feedback, and development plans.
• Create a collaborative and inclusive team environment where reps are motivated to exceed goals and support one another.

Cross-Functional Alignment:

• Partner with Marketing, Sales Enablement, Product, and Customer Success teams to deliver tailored messaging and enablement for enterprise prospects in the region.
• Act as a feedback loop between the field and product/leadership to help shape Freshworks’ competitive positioning in large enterprise accounts.
• Ensure enterprise customer experience is consistent, high-quality, and aligned with Freshworks’ values.

Please note: This is a remote role open to applicants in the Central U.S., with a preference for Chicago IL or Austin TX

Qualifications

Experience:

• 10+ years in SaaS or enterprise technology sales, with 3–5+ years in a front-line leadership role managing enterprise sellers.
• Strong & demonstrable track record of success selling into Fortune 1000 / Global 2000 accounts within the Central U.S. region.
• Proven ability to manage and coach teams through complex, high-value, multi-year deals.

Expertise:

• Deep familiarity with MEDDIC or similar qualification frameworks and how to apply them at scale.
• Experience selling ITSM, CX, CRM, or EX solutions with an understanding of enterprise buying committees and procurement cycles.
• Proficient in Salesforce and other modern sales tech stacks (e.g. Clari, Outreach, Gong, etc.).

Leadership Behaviors:

• Customer-Obsessed: Advocate relentlessly for the enterprise customer while driving internal alignment to their needs.
• Disciplined Operator: Bring process, structure, and predictability to your team’s day-to-day operations.
• Team Builder: Develop a strong leadership bench through mentorship, accountability, and talent development.
• Strategic Thinker: Balance near-term execution with long-term planning to ensure scalable growth
• Coach at Heart: Champion field enablement, deal reviews, and learning loops to grow your reps and improve win rates.
  
  

Additional Information

The annual base salary range for this position is $204,700 — $235,900 USD + Sales Variable

Compensation is based on a variety of factors including but not limited to location, experience, job-related skills, and level.

Freshworks offers multiple options for dental, medical, vision, disability and life insurances. Equity + ESPP, flexible PTO, flexible spending, commuter benefits and wellness benefits are also offered. Freshworks also offers adoption and parental leave benefits.

At Freshworks, we are creating a global workplace that enables everyone to find their true potential, purpose, and passion irrespective of their background, gender, race, sexual orientation, religion and ethnicity. We are committed to providing equal opportunity for all and believe that diversity in the workplace creates a more vibrant, richer work environment that advances the goals of our employees, communities and the business.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Human Resources

• Industries

  IT Services and IT Consulting

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