Director, Sales (Relocate to Puerto Rico)

We are seeking a Director of Sales who will lead our new business and account management organizations to accelerate revenue growth, strengthen customer retention, and expand existing accounts across the BOLD portfolio based in Puerto Rico. You will directly manage two Sales Managers and provide leadership to a broader team of Account Managers, Senior Account Executives, and Account Executives.

You will be responsible for establishing a consistent sales operating model, improving team quota attainment, and overseeing the performance of the customer portfolio. You will also partner with cross-functional leaders to strengthen pipeline health, improve the customer experience, and translate market insights into effective go-to-market strategies.

About this team 

We are an evolving sales organization with the energy and pace of a startup, supported by the global recognition of Monster and CareerBuilder. Our team operates both remotely across various geographies and in a hybrid model out of our Guaynabo headquarters.

Our organization brings together outbound sales professionals focused on new customer acquisition and consultative account managers responsible for retention, renewals, and expansion. We are highly accountable, results-oriented, and committed to reclaiming market share through disciplined execution and exceptional customer partnership.

What you'll do

•    Sales and Account Management Leadership: Lead and coach 2 Sales Managers responsible for new business acquisition and customer retention, renewal, and expansion across SMB, Mid-Market, and Enterprise segments.
•   New Business Growth: Oversee the full sales cycle for net-new customer acquisition and ensure Account Executives and Senior Account Executives consistently achieve monthly and quarterly performance goals.
•   Retention and Expansion: Drive the strategies and operating rhythms needed to protect recurring revenue, improve customer retention, and identify expansion opportunities within existing accounts.
•   Sales Execution: Develop and continuously improve sales playbooks, messaging, scripts, discovery practices, and consultative objection-handling strategies.
•   Performance Management: Establish clear expectations and reinforce accountability through data-driven scorecards, pipeline reviews, forecasting, coaching, and structured performance discussions.
•   Portfolio Oversight: Monitor the health and performance of the aggregate customer portfolio, including revenue attainment, retention, expansion, customer concentration, and account risk.
•   Pipeline and Forecast Management: Maintain strong pipeline discipline and data integrity in Salesforce while improving forecast accuracy, conversion rates, sales velocity, and coverage.
•   Cross-Functional Partnership: Collaborate with Product, Marketing, Customer Success, Operations, and Engineering to share customer and market insights and shape go-to-market priorities.
•   Business Planning: Develop and present sales plans, revenue forecasts, resource recommendations, and performance updates to senior and executive leaders.

What you'll need

•  B2B Sales Experience: Experience balancing high-volume, high-activity sales execution with Mid-Market or Enterprise deal complexity.
•   Sales Leadership: 10 or more years of progressive B2B sales experience, including significant experience leading sales teams.
•   People Leadership: Demonstrated success leading managers and building high-performing teams across both new business acquisition and account management.
•   Quota Attainment: A track record of achieving multi-million-dollar team revenue targets and improving performance in complex or evolving sales environments.
•   Retention and Growth Expertise: Experience developing strategies that improve customer retention, renewals, account expansion, and overall portfolio performance.
•   Financial and Commercial Acumen: Strong analytical skills and the ability to connect customer acquisition metrics, including CPA and CPC, with customer ROI, revenue performance, and profitability.
•   Sales Operations Discipline: Deep experience using CRM platforms, preferably Salesforce, to manage pipelines, forecasts, activity metrics, and structured sales KPIs.
•   Leadership and Communication: Strong executive presence, sound judgment, and the ability to communicate business plans, performance results, and recommendations to senior stakeholders.

What's good to have 

•   Industry Experience: Experience in job boards, recruitment advertising, ATS platforms, staffing, digital marketplaces, or other technology-enabled business services.
•   B2B SaaS Environment: Experience working in B2B SaaS Sales.
•   Operating Frameworks: Familiarity with structured decision-making and accountability frameworks such as RACI, DACI, or RAPID.
•   Scaling Experience: Experience launching a new regional sales operation, integrating sales teams, or establishing foundational processes in a growing organization.
•   Compensation Design: Experience partnering with HR, Finance, and Sales Operations to develop or scale sales incentive and compensation plans.
•   Organizational Transformation: Experience improving the performance of an established sales organization through stronger leadership routines, process discipline, coaching, and accountability.

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.

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