Senior Technical Project Manager

Senior Technical Project Manager, Healthcare

Remote, U.S. (Los Angeles preferred)

About Us

Sidebench is a healthcare digital transformation firm that designs, builds, and scales digital products and data platforms for leading health companies and high-growth ventures. We bring together four strengths in a single team: enterprise technology & product strategy, UX-first product design, pragmatic systems and data architecture, and secure, HIPAA-compliant engineering. Our integrated approach moves us from strategy to delivery fast, delivering the first measurable win and building toward sustainable competitive advantage.

We are chosen by enterprise digital transformation leaders and founding teams to solve the hardest product and data problems. Our process aligns product, tech architecture, data, design, and strategy experts to accelerate decisions and reduce risk. 

At Sidebench, you'll work with smart, collaborative teammates who care about impact, craftsmanship, and continuous learning, while helping shape the future of healthcare and digital products.

Why this role matters

You will be a high-velocity TPM who owns delivery for multiple, high-impact healthcare engagements from discovery to launch. This is a rapid-growth role for someone who wants deep, hands-on ownership, direct client exposure, and the chance to shape new products and business lines that improve care.

Sidebench values relentless drive, humility, ownership, and results. We hire people who move quickly, learn continuously, and are team-first.

Impact and scope you will own

• Own 2 to 4 concurrent healthcare technology engagements. Accountability includes timeline, budget, scope, quality, and client satisfaction.
• Own scoping, estimation, and solution shaping for the proposals you deliver. Be the named delivery lead on SOWs.
• Lead client workshops, steering meetings, sprint planning, backlog prioritization, and risk mitigation.
• Own project financials: forecasting, burn, change control, and escalation.

Day in the life

Run executive steering with client stakeholders, lead cross-functional sprint planning with product, design, and engineering, produce crisp status and decision materials, run client workshops, and coach teammates on delivery plans. You will switch between strategy and scoping and hands-on execution.

Who you are - required signals

• 3+ years in technical project management or consulting, delivering custom software projects, with clear career progression and ownership examples.
• At least one end-to-end healthcare project or 2+ years in healthcare-adjacent work with transferable outcomes.
• Experience managing project budgets and roadmaps for work in the $200k-$2M range.
• Technical fluency: able to understand architecture tradeoffs, evaluate APIs, and assess integration risk. Comfortable with Jira, Confluence, and product discovery practices.
• Client-facing leadership: ran workshops and maintained executive relationships.
• Measured impact: can describe quantified outcomes you drove and how you achieved them.

Strong pluses

• HIPAA, HITRUST, or clinical workflow experience.

• Pre-sales experience: scoping, estimation, SOW creation.

• SQL and cloud literacy, experience integrating EHR systems.

• AI-forward mindset with hands-on experience using automation or LLM-based tools to support delivery. Candidates should be comfortable discussing how theyve applied these tools in real workflows and the impact on speed, quality, or team effectiveness.

Interview process and evaluation

We follow a rigorous and transparent process to identify high-potential hires. Typical stages:

1. Hiring manager screen - 20 to 30 minutes.

2. Take-home Project - 60 minutes.
3. Panel interview - delivery playbook, technical fluency, and client simulation.

4. Reference checks and culture/values interview.

Candidates will be evaluated on technical fluency and risk judgment, outcome orientation and metrics-driven delivery, client engagement leadership, and culture fit (hunger, humility, grit, team-first).

This is not for you if

You prefer rigid, low-ambiguity roles or manage only ceremonies without owning delivery outcomes. If you are not excited by direct client work, multiple concurrent projects, and hands-on scoping, then this is NOT the right role.

How to apply

Please submit:

1. Resume.

2. Short portfolio: 2-3 engagements you led with measurable outcomes (total 500 words). For each, include your role, approx budget, timeline, biggest area of complexity/risk and mitigation, and any outcomes.
3. A 250-word note explaining why you are taking a leap now and how you want to grow at Sidebench.

Applications without the portfolio will be deprioritized.

Total Compensation

Sidebench offers rapid career advancement and significant ownership of both product and business initiatives for high-achieving individuals.

Total Comp Range: $120,000–$200,000