Sales Enablement Specialist

The role

You will lead internal enablement for BOLD's B2B Sales team. You will build and deliver onboarding, training, messaging, playbooks, and coaching to improve seller readiness and execution.

What you will do

• Lead internal onboarding and ongoing training for Sales team success.
• Develop and maintain standardized messaging, playbooks, call guides, and competitive materials.
• Partner with Sales leaders and Sales Operations to identify skill gaps using performance data.
• Facilitate workshops, role-play sessions, and coaching on sales conversations and win-back strategies.
• Work with Marketing and Sales leaders to ensure content reflects approved messaging and business priorities.
• Partner with the Adoption & Enablement Specialist to incorporate customer training insights.
• Track win-back results and sales program win rates to evaluate program impact.

Required qualifications

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

Nice to have

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

Benefits

• 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
• Medical, dental, and vision
• Life & long-term disability insurance
• Mental health support and resources
• Wellness reimbursement
• Flexible PTO, sick time, and observed holidays

Before you apply

• This position requires the candidate to work in Puerto Rico.
• Applicants must currently reside in Puerto Rico or be willing to relocate there.

About the company

BOLD is an established global organization that helps people find jobs through digital products. The company creates tools to help people build resumes, cover letters, and CVs.