Head of Sales Enablement

1 Month ago • 8 Years + • Sales

Job Summary

Job Description

The Head of Sales Enablement will lead the development and execution of sales enablement programs. Responsibilities include creating training programs, content, and tools to improve sales effectiveness, optimizing the sales process, integrating acquired products, collaborating with cross-functional teams, and analyzing sales performance. The role requires aligning sales enablement initiatives, providing feedback on product development and marketing strategy, and leading and developing a sales team. The ideal candidate should have extensive experience in B2B enterprise software sales enablement, especially in a high-growth, technology-driven environment and experience integrating acquired products. The role also includes reporting on the impact of sales enablement initiatives, ensuring sales teams are equipped with up-to-date product knowledge, competitive insights, and buyer personas to maximize their effectiveness throughout the sales cycle.
Must have:
  • 8+ years sales enablement experience in B2B enterprise software.
  • Experience integrating acquired products into sales motions.
  • Deep understanding of the sales process.
  • Experience in developing and delivering training programs.
Good to have:
  • Experience with CRM tools (Salesforce preferred).
  • Experience in a fast-growing, disruptive tech company.
  • Familiarity with investment management or financial technology.
Perks:
  • Business casual atmosphere in a flexible working environment
  • Team focused culture that promotes innovation and ownership
  • Access cutting edge investment reporting technology and expertise
  • Defined and undefined career pathways
  • Competitive medical, dental, vision, and life insurance benefits
  • Maternity and paternity leave
  • Personal Time Off and Volunteer Time Off
  • RSUs as well as employee stock purchase plan and 401k with match
  • Work from anywhere 3 weeks out of the year
  • Work from home Fridays

Job Details

Role Overview:
We are seeking a strategic, results-oriented Head of Sales Enablement to join our global Revenue Operations team. This leader will drive the development and execution of sales enablement programs that accelerate sales productivity, enhance go-to-market strategies, and integrate acquired company products into Clearwater’s sales motions. The ideal candidate will have extensive experience in B2B enterprise software sales enablement, particularly in a high-growth, technology-driven environment, and a proven track record in successfully onboarding and integrating new product lines post-acquisition.

Key Responsibilities:

Sales Enablement Strategy & Execution:

  • Expand Clearwater’s existing enablement program to develop and implement a comprehensive sales enablement strategy that aligns with Clearwater’s revenue growth objectives.

  • Lead the creation and execution of training programs, content, tools, and resources that clearly articulate Clearwater’s value proposition, driving sales effectiveness and enabling sales teams to engage with prospects and customers with confidence and impact.

  • Ensure sales teams are equipped with up-to-date product knowledge, competitive insights, and buyer personas to maximize their effectiveness throughout the sales cycle.

Sales Process Optimization & Integration:

  • Partner with the Product and Marketing teams to define and streamline the sales process, ensuring it aligns with customer needs and market trends.

  • Lead the integration of acquired products into Clearwater’s existing sales motions, ensuring a seamless and effective go-to-market strategy that maximizes revenue opportunities.

  • Develop and refine sales playbooks and processes to ensure smooth execution and scalability post-acquisition.

Cross-functional Collaboration:

  • Work closely with the Sales Leadership team to align sales enablement initiatives with company priorities and objectives.

  • Partner with Revenue Operations, Marketing, and Product teams to ensure the sales team is aligned with the overall business strategy and product roadmap.

  • Provide feedback and insights from the field to help inform product development, marketing strategy, and sales training.

Sales Performance Analytics & Reporting:

  • Define and track key performance metrics related to sales enablement efforts and continuously optimize programs based on data and feedback.

  • Regularly report on the impact of sales enablement initiatives, including improvements in sales productivity, ramp times, win rates, and overall sales performance.

Team Leadership & Development:

  • Drive a high-performance environment that encourages innovation, creativity, and a deep understanding of the sales function.

Qualifications:

  • Proven experience (8+ years) in sales enablement within B2B enterprise software, with a strong background in SaaS or technology companies.

  • Experience integrating acquired products into established sales motions and driving cross-functional alignment post-acquisition.

  • Deep understanding of the sales process, including prospecting, qualification, negotiation, and closing strategies.

  • Strong background in developing and delivering training programs, sales content, and tools that have demonstrable impact on sales performance.

  • Excellent communication, presentation, and interpersonal skills, with the ability to influence at all levels of the organization.

  • Analytical mindset with the ability to use data to drive decisions and measure success.

  • Proven leadership experience, with the ability to manage and inspire a team in a fast-paced, high-growth environment.

  • Strong project management skills and experience driving complex initiatives across multiple teams.

  • Willingness and ability to work from the office either in Boise, ID or New York, NY four days a week

Preferred Qualifications:

  • Experience with CRM tools (Salesforce preferred) and sales enablement platforms.

  • Previous experience working in a fast-growing, disruptive tech company.

  • Familiarity with investment management or financial technology is a plus.

What we offer:

  • Business casual atmosphere in a flexible working environment 

  • Team focused culture that promotes innovation and ownership 

  • Access cutting edge investment reporting technology and expertise

  • Defined and undefined career pathways allowing you to grow your own way 

  • Competitive medical, dental, vision, and life insurance benefits

  • Maternity and paternity leave 

  • Personal Time Off and Volunteer Time Off to give back to the community

  • RSUs as well as employee stock purchase plan and 401k with match  

  • Work from anywhere 3 weeks out of the year 

  • Work from home Fridays

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About The Company

Clearwater Analytics (NYSE: CWAN) is the leading provider of web-based investment portfolio accounting, reporting, and reconciliation services for institutional investors at thousands of organizations.


Clearwater aggregates, reconciles, and reports on more than $6.4 trillion in assets across thousands of accounts daily. Our clients include corporate treasuries, insurance companies, investment managers, banks, governments, and other institutional investors both in the United States and worldwide.


For more than a decade, we have leveraged web-based software and world-class client service to help clients such as American Family Insurance, Arch Capital, C.V. Starr & Co., Cisco, Facebook, Oracle, Selective Insurance, Sirius Group, Sompo International, Starbucks, WellCare Health Plans, Wilton Re, and many others, streamline their investment and accounting operations. Clearwater also works with hundreds of custodians, investment managers, dealers/brokers, and electronic trading portals who offer Clearwater to their many clients.


With global headquarters in Boise, Idaho, and offices in Edinburgh, Frankfurt, London, New Delhi, New York, Paris, Seattle, Singapore, and Washington D.C., Clearwater sets the new global standard for investment portfolio reporting.

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