Sales Enablement Director

Come join Deepwatch’s team of world-class cybersecurity professionals and the brightest minds in the industry. If you're ready to challenge yourself with work that matters, then this is the place for you. We're redefining cybersecurity as one of the fastest growing companies in the U.S. – and we have a blast doing it!

Who We Are

Deepwatch is the leader in managed security services, protecting organizations from ever-increasing cyber threats 24/7/365. Powered by Deepwatch’s cloud-based security operations platform, Deepwatch provides the industry’s fastest, most comprehensive detection and automated response to cyber threats together with tailored guidance from dedicated experts to mitigate risk and measurably improve security posture. Hundreds of organizations, from Fortune 100 to mid-sized enterprises, trust Deepwatch to protect their business. 

Our core values drive everything we do at Deepwatch, including our approach to tackling tough cyber challenges. We seek out tenacious individuals who are passionate about solving complex problems and protecting our customers. At Deepwatch, every decision, process, and hire is made with a focus on improving our cybersecurity solutions and delivering an exceptional experience for our customers. By embracing our values, we create a culture of excellence that is dedicated to empowering our team members to explore their potential, expand their skill sets, and achieve their career aspirations, which is supported by our unique annual professional development benefit.

Deepwatch Recognition Includes:

• 2025, 2024, 2023, 2022 and 2021 Great Place to Work® Certified
• 2024 Military Times Best for Vets Employers
• 2024 US Department of Labor Hire Vets Gold Award
• 2024 Forbes' America's Best Startup Employers
• 2024 Cyber Defense Magazine, Global Infosec Awards 
• 2023 and 2022 Fortress Cybersecurity Award
• 2023 $180M Series C investment from Springcoast Capital Partners, Splunk Ventures, and Vista Credit Partners of Vista Equity Partners
• 2022 Cybersecurity Excellence Award for MDR

Reporting to the CRO, the Sales Enablement Director is responsible for developing comprehensive, scalable onboarding and training programs for all existing and new sales hires that will accelerate time to productivity and enable Deepwatch to achieve its goals. 

The primary aim of this role is to collaborate with Sales, Marketing, Product Management, Customer Success, and Operations to develop a systematic approach to improve the efficiency and effectiveness of the sales organization. The ideal candidate is detail-oriented, collaborative, a strong communicator, and passionate about working with employees to help them excel.  Your role will provide excellent sales insight and training to the team and help accelerate our path to redefining an exciting industry.

In this role, you’ll get to:

Sales Enablement Strategy & Leadership

• Define and execute a global sales enablement strategy aligned with Deepwatch’s GTM objectives.
• Build scalable onboarding, training, and coaching programs to ramp new sellers quickly and improve productivity across the sales organization.
• Partner with sales leadership to define core competencies, develop skill frameworks, and establish consistent performance expectations.
• Own sales communication and release management programs
• Support Sales Kickoff and Leader Offsites by helping manage and build content for sales enablement breakouts 

Training & Content Development

• Design, deliver, and maintain training programs, including new hire onboarding, product/solution training, and ongoing skills development
• Develop and deliver compelling training material with Subject Matter Experts to align Go To  Market  messaging  to sales solutions
• Create and curate compelling sales content, playbooks, and tools that support consultative, value-based selling
• Ensure all enablement resources are easy to access, up-to-date, and aligned with the buyer’s journey
• Partner with the Learning & Development team to build comprehensive plans within the  Learning Management System (LMS) (communications, training, knowledge checks, etc.) to support knowledge retention and enhance our onboarding and sales training curriculum, ensuring alignment with evolving sales strategies

Sales Tools & Process Optimization

• Own the strategy and adoption of sales enablement tools (e.g., CMS, LMS, sales intelligence platforms) in partnership with Sales Operations
• Standardize and improve sales processes, including account planning, opportunity management, and proposal development
• Partner with Marketing and Product teams to translate messaging into field-ready assets that resonate with customers and partners

Collaboration & Cross-Functional Alignment

• Work closely with Channel and Partner teams to align enablement programs for both direct and indirect sales motions
• Work with Sales Leadership and Revenue Operations to determine sales skills and/or product knowledge gaps where training would make an impact
• Partner with Product Management and Product Marketing to ensure the sales team is equipped with the latest competitive intelligence, product updates, and market insights
• Serve as a trusted advisor to leadership, surfacing insights and recommendations that improve execution and results

Performance & Measurement

• Define key enablement KPIs to measure program effectiveness and seller productivity
• Track and report on the impact of enablement initiatives (e.g., ramp time, win rates, deal velocity, quota attainment).
• Continuously refine enablement strategy based on data, feedback, and evolving business priorities
• Measure, analyze, and report the impact of onboarding programs on key productivity indicators
• Leverage your quantitative skills to interpret data, gain insights, and then translate them into actionable improvements

To be successful in this role, you’ll need to:

• 10+ years of experience in sales enablement, sales operations, or sales leadership, ideally within cybersecurity, SaaS, or managed services
• Strong understanding of consultative, solution-based selling methodologies (e.g., Challenger, MEDDICC, SPIN, or similar).
• Leverage your knowledge and hands-on experience in sales environments to develop a systematic approach that improves the efficiency and effectiveness of the Sales organization
• Convert sales best practices and concepts into content form that Learning and Development can use to design training programs
• Maintain enterprise calendar of new hires and ongoing training to track progress through learning activities, milestones, and assessments to ensure new hires are meeting benchmarks and to assess Sales readiness and learning/development needs
• Accurately determine if performance gaps can be closed via training and monitor performance improvement associated with training provided 
• Demonstrate persuasive communication and the ability to influence at all levels to acquire training content in partnership with Sales, Marketing, Product Management, and Customer Success Teams 
• Strong analytical skills with experience defining and tracking enablement metrics.
• Be collaborative, proactive, and adaptable, with a passion for developing talent and driving measurable results
• Demonstrated ability to translate complex technical solutions into compelling, value-based narratives for sellers and buyers.
• Experience managing enablement platforms (e.g., Highspot, Gong, 6sense, ZoomInfo, Sales Navigator) and CRM systems (Salesforce preferred).
• Bachelor’s degree or equivalent experience required; advanced degree or certifications in enablement, sales, or related fields a plus.

Statutory Pay Disclosure

The anticipated salary range for this role is $179,000 - $213,000 + bonus + stock options + benefits. Actual compensation may vary from posted hiring range based upon geographic location, work experience, education, and/or skill level.

What We Offer:

Deepwatch is excited to provide benefits designed to support team members and their families. Including:

• Medical, dental, vision, and disability insurance
• Flexible Time Off (FTO), 9 company holidays, sick leave and 8-Weeks Paid Parental Leave
• Unique professional development benefits, starting at $3,000 annually
• Wellness contests and monthly educational programs
• 401(K) retirement program with employer match
• Learn more here: Deepwatch Benefits

We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don’t hesitate to apply — we’d love to hear from you.  Please review our DEI Statement here.

Deepwatch welcomes and encourages applications from people with disabilities and accommodations are available on request for candidates taking part in all aspects of the selection process. Please inform your recruiter or contact recruiting@deepwatch.com for further information.   All Deepwatch employees are expected to:

• Be interested in and able to work remotely from a home office when not at a corporate office
• Pass a pre-employment background check in accordance with applicable laws

Deepwatch is an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, age, disability status, marital status, sexual orientation, gender identity, genetic information, protected veteran status, or any other characteristic protected by law.  In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.

By submitting your application, you agree that Deepwatch may collect your personal data for recruiting, global organization planning, and related purposes. The Deepwatch Privacy Policy explains what personal information we may process, where we may process your personal information, our purposes for processing your personal information, and the rights you can exercise over Deepwatch’s use of your personal information.