Sales Enablement Specialist

We are seeking a Sales Enablement Specialist to lead internal enablement for BOLD's B2B Sales team. You will build and deliver onboarding, ongoing training, messaging, playbooks, and coaching that strengthen seller readiness and improve execution. You will use performance data to identify skill gaps and measure program effectiveness, with a focus on win-back results and sales program win rates. You will work closely with Sales leaders, Sales Operations, Marketing, and the Adoption & Enablement Specialist to ensure training reflects both business priorities and the customer experience.

About This Team

The Sales Operations team equips our B2B Sales organization with the processes, tools, insights, and training needed to perform effectively. We work closely with Sales, Marketing, and post-sale partners to turn business priorities and customer feedback into practical programs for the Sales team. The team is collaborative, hands-on, data-informed, and focused on continuous improvement.

What You’ll Do

• Sales Onboarding and Development: Lead internal onboarding and ongoing training that build the skills, knowledge, and confidence needed for Sales team success.
• Enablement Content: Develop and maintain standardized messaging, playbooks, call guides, objection-handling resources, and competitive materials for the Sales team.
• Capability Assessment: Partner with Sales leaders and Sales Operations to use performance data and field feedback to identify skill gaps and prioritize enablement needs.
• Training and Coaching: Facilitate workshops, role-play sessions, and coaching on sales conversations, win-back strategies, product value, and other priority topics.
• Cross-Functional Alignment: Work with Marketing, Sales leaders, and subject matter experts to ensure enablement content reflects approved messaging, processes, and business priorities.
• Customer Experience Insights: Partner with the Adoption & Enablement Specialist to incorporate customer training insights and coordinate select product-specific sessions, such as best practices for using resume search, while maintaining primary ownership of internal Sales enablement.
• Program Measurement: Track win-back results and sales program win rates to evaluate program impact and continuously improve training and resources.

What You’ll Need

• Experience: 4+ years of experience in Sales Enablement, Sales Training, Sales Operations, or a related B2B sales function.
• Program Development: Experience designing and delivering onboarding, ongoing training, and enablement programs for B2B sales teams.
• Sales Knowledge: Strong understanding of B2B sales cycles, seller workflows, and the skills needed to support new business, retention, and win-back efforts.
• Content Development: Ability to turn complex product, process, and sales information into clear, practical training materials and playbooks.
• Facilitation and Coaching: Strong presentation, workshop facilitation, role-play, and coaching skills for both new and experienced sales professionals.
• Data and Measurement: Ability to interpret sales performance data, identify trends, and use KPIs to evaluate and improve enablement programs.
• Tools and Collaboration: Proficiency with CRM systems such as Salesforce or HubSpot and the ability to work effectively across Sales, Sales Operations, and Marketing.

What's Good to Have

• Industry Experience: Experience in recruitment, staffing, professional services, or HR technology.
• Sales Experience: Prior experience as an Account Executive, Account Manager, or Business Development professional in a B2B environment.
• Sales Methodologies: Familiarity with structured sales methodologies such as Challenger or MEDDIC.
• Enablement Technology: Experience with learning management systems, content platforms, or sales enablement tools.
• Customer Adoption Partnership: Experience partnering with Customer Success, product adoption, or client training teams.

Benefits

Outstanding Compensation

• Competitive salary
• Bi-annual bonus
• 401(k) plan with match
• Equity in company
• Flexible spending accounts (health, dependent care)
• Internet and home office reimbursement
• In-office catered breakfast and lunches

100% Full Health Benefits

• Medical, dental, and vision (optional plans for your family)
• Life & long-term disability insurance (optional)
• Mental health support and resources
• Wellness reimbursement (gym, health apps, etc.)
• Pet Insurance (optional)

Flexible time away

• Flexible PTO
• Sick time policy
• Observed holidays

Certain group health plans are required to disclose on a public website information regarding in-network provider rates and historical out-of-network allowed amounts and billed charges for covered items and services in two separate machine-readable files (MRFs). The MRFs for the Triple S Salud medical benefit plans are linked below as of July 1, 2022:

https://salud.grupotriples.com/en/transparency-in-coverage-machine-readable-files/

ELIGIBILITY

LOCATION

This position requires the candidate to work in Puerto Rico. We welcome applicants who currently reside in Puerto Rico or those willing to relocate there.