Senior Project Manager I

We are seeking a Senior Project Manager I to lead complex, cross-functional initiatives spanning multiple business units. In this role, you’ll drive high-visibility projects from planning through delivery with a focus on balancing scope, velocity, and quality while navigating cross-team dependencies and risk. You measure yourself on what shipped, not on how complete the tracker looked. When process and delivery pull against each other, you make the call, name the tradeoff out loud, and keep the team moving rather than waiting for the framework to resolve it.

About This Team

Within our broader Product Technology group, which builds the technology and data intelligence powering internal partners and scaling our customer base, the Program Management team serves as the connective tissue for our most critical strategic initiatives.

As a Senior Project Manager, you will join a high-impact team dedicated to driving operational excellence, aligning cross-functional partners, and ensuring our technical roadmaps are delivered efficiently. We foster a collaborative, transparent culture where structure meets innovation, empowering our teams to turn complex technical visions into measurable results.

What You’ll Do

Project Execution & Delivery

Lead and deliver large, complex projects or small programs spanning multiple business units with clear scope, moderate ambiguity, and predictable results.

Cross-Team Alignment & Blocker Removal

Lead multi-team execution while keeping a sharp focus on project goals, removing systemic blockers, and maintaining alignment through delivery.

Structured Stakeholder Communication

Communicate with well-structured messaging to ensure full transparency, alignment, and focus across stakeholders. Proactively frame trade-offs, clarify decisions, and influence discussions using data.

Partnership & Conflict Resolution

Build high-trust partnerships across functions. Resolve minor conflicts independently and mediate team dynamics with clear ownership.

Risk Management & Mitigation

Anticipate project roadblocks, risks, and scope creep early, lead identification and root-cause analysis across complex initiatives, and escalate decision-making/trade-offs to ensure timely solutions meet overall goals.

Strategic Roadmap Alignment

Connect project plans to stakeholder and business outcomes, driving prioritization discussions while balancing value versus effort.

Process Navigation & Adaptability

Navigate cross-functional department processes efficiently, leading teams through complex change and uncertainty with clarity and professionalism.

Operational Optimization

Optimize the use of project management tools and workflows (Jira, JPD, Confluence) to improve workflow clarity, delivery predictability, and quality across multiple teams.

What You’ll Need

Proven Track Record

5+ years of experience successfully managing medium to large, complex projects or small programs with cross-functional dependencies and high visibility through to timely completion.

Tactical Autonomy

Ability to operate with high tactical independence, proactively defining execution steps within established frameworks and seeking guidance primarily for strategic or complex conflicts.

Methodology Fluency Without Attachment

• Deep working knowledge of Agile, Scrum, Kanban, and SDLC workflows, paired with the judgment to right-size them. You pick the lightest process that still produces a predictable outcome, adjust when the situation changes, and can explain why you dropped a ceremony as clearly as why you added one. Certifications are welcome, orthodoxy is not
• .

Tooling & Process Proficiency

Strong hands-on experience setting up and optimizing PM tools (Jira, Jira Product Discovery, Confluence) for boards, documentation, and reporting artifacts. Proficiency in Google Suite (Sheets, Docs), Slack, and Zoom.

Business Acumen & Analytical Thinking

Solid understanding of business objectives and project KPIs to shape execution plans and evaluate operational risks/impacts.

Cross-Functional Collaboration

Demonstrated ability to build relationships across teams, align stakeholders with competing goals, and drive accountability without direct authority. Exceptional communication while working directly with executive leadership and C-suite stakeholders, providing concise status updates and managing expectations.

Meeting Facilitation Mastery

Proven track record of running efficient, productive, and structured project meetings ensuring clear agendas, mitigating tangents, and actionable outcomes.

Continuous Improvement Leadership

Experience identifying operational and technical gaps, introducing just enough structure to resolve them without creating bureaucratic friction or slowing the team down.

Nice to Have

Subject Matter Expertise

Acting as a subject matter expert in project management practices within your department or team.

PM Mentorship & Standardization

Experience mentoring junior or mid-level project managers, contributing to internal project management capability building, or helping establish standardized delivery templates and guidelines.

Peer Knowledge Sharing

Track record of sharing best practices, tools, and domain insights to elevate the capabilities of adjacent team members.

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/

Please only add this section to select PR roles open to US candidates.

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.

SELECT ONE: #LI-Hybrid

About Bold

We Transform Work Lives

As an established global organization, BOLD helps people find jobs. Our story is one of growth, success, and professional fulfillment. We create digital products that have empowered millions of people in 180 countries to build stronger resumes, cover letters, and CVs. The result of our work helps people interview confidently, finding the right job in less time. Our employees are experts, learners, contributors, and creatives.

We Celebrate And Promote Diversity And Inclusion

• We value our position as an Equal Opportunity Employer. We hire based on qualifications, merit, and our business needs. We don't discriminate regarding race, color, religion, gender, pregnancy, national origin or citizenship, ancestry, age, physical or mental disability, veteran status, sexual orientation, gender identity or expression, marital status, genetic information, or any other applicable characteristic protected by law.
• Under San Francisco's Fair Chance Ordinance, qualified applicants with arrest and conviction records will be considered for the position.