Director, Sales

BOLD

BOLD sales director leading new-business and account-management teams for its global employment products. Driving revenue growth, retention, expansion, forecasting, and go-to-market execution from Puerto Rico.

Posted 8/5/2026full-timeGuaynabo • 🇺🇸 United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in B2B sales leadership, focusing on new business acquisition, customer retention, and account management. Proven ability to develop strategies that enhance portfolio performance and drive revenue growth while utilizing CRM tools like Salesforce for effective pipeline management.

Highest-signal resume keywords

B2B Sales LeadershipSalesforce CRM ProficiencyCustomer Retention StrategiesHigh-Performing Team DevelopmentRevenue Forecasting

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Cycle ManagementPerformance Goal AchievementSales Playbook DevelopmentPipeline ReviewForecast Accuracy ImprovementAccount Risk MonitoringSales Velocity OptimizationObjection-Handling StrategiesRevenue Attainment TrackingActivity Metrics Analysis

Soft Skills

CoachingAnalytical SkillsExecutive PresenceCommunication SkillsSound Judgment

Industry Keywords

SMBMid-MarketEnterpriseCustomer SuccessGo-To-Market StrategyAccount ManagementSales KPIsRevenue PerformanceCustomer InsightsPuerto Rico Residency

About the role

Key responsibilities & impact

Lead and coach 2 Sales Managers responsible for new business acquisition, customer retention, renewals, and expansion across SMB, Mid-Market, and Enterprise segments
Oversee the full sales cycle for net-new customer acquisition and ensure Account Executives and Senior Account Executives achieve performance goals
Drive strategies and operating rhythms to protect recurring revenue, improve retention, and identify expansion opportunities
Develop and improve sales playbooks, messaging, scripts, discovery practices, and objection-handling strategies
Establish expectations and accountability through scorecards, pipeline reviews, forecasting, coaching, and performance discussions
Monitor customer portfolio health, including revenue attainment, retention, expansion, customer concentration, and account risk
Maintain pipeline discipline and Salesforce data integrity while improving forecast accuracy, conversion rates, sales velocity, and coverage
Collaborate with Product, Marketing, Customer Success, Operations, and Engineering on customer insights and go-to-market priorities
Develop and present sales plans, revenue forecasts, resource recommendations, and performance updates to senior and executive leaders

Requirements

What you’ll need

Experience balancing high-volume, high-activity B2B sales execution with Mid-Market or Enterprise deal complexity
10 or more years of progressive B2B sales experience, including significant experience leading sales teams
Demonstrated success leading managers and building high-performing teams across new business acquisition and account management
Track record of achieving multi-million-dollar team revenue targets and improving performance in complex or evolving sales environments
Experience developing strategies for customer retention, renewals, account expansion, and portfolio performance
Strong analytical skills and ability to connect CPA and CPC with customer ROI, revenue performance, and profitability
Deep experience using CRM platforms, preferably Salesforce, to manage pipelines, forecasts, activity metrics, and sales KPIs
Strong executive presence, sound judgment, and ability to communicate business plans, performance results, and recommendations to senior stakeholders
Residents of Puerto Rico or US citizens willing to relocate to Puerto Rico

Benefits

Comp & perks

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 (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 PTO
Sick time policy
Observed holidays