Upwork

Director, Strategic Initiatives & Special Projects

Upwork$154K — $254K *
US-AnywhereRemote in United States
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-10 years of experience in strategic initiatives or project management
  • Strong understanding and passion for AI applications in business
  • Proven ability to make data-driven decisions in ambiguous situations
  • Experience in driving revenue growth and operational efficiency
  • Demonstrated success in cross-functional collaboration

Responsibilities

  • Identify high-leverage opportunities across the business
  • Transform ambiguity into structured execution
  • Act decisively with minimal guidance
  • Challenge assumptions and engage in tough discussions
  • Build sustainable systems for lasting impact
  • Lead initiatives that effectively leverage AI for growth

Benefits

  • Comprehensive medical coverage for you and your family
  • Unlimited PTO
  • 401(k) plan with matching
  • 12 weeks of paid parental leave
  • Opportunities for rapid personal and career growth
Full Job Description
The Director, Strategic Initiatives & Special Projects will work directly with the GM on high-impact initiatives that drive revenue growth and operational efficiency across Lifted. This role operates across all business functions. Projects can span teams, workflows, or business areas where solving problems can materially drive growth or improve efficiency. You will operate without full information, make decisions decisively, and take full ownership of the outcomes (good and bad).

A core focus: AI is a key lever in this role. You have a proven track record of applying AI to solve business challenges, identifying high-impact opportunities, and delivering measurable results.

Work directly with the GM on high-impact initiatives that drive revenue growth and operational efficiency across Lifted. This role is not tied to a single function and is focused on building and launching new solutions. Projects can span any team, workflow, or problem where meaningful growth or efficiency can be created. You will operate without full information, make decisions decisively, and take full ownership of the outcomes (good and bad).

AI is a central lever in this role. You should be curious, pragmatic, and focused on applying it in ways that drive measurable business impact.

Work directly with the GM on high-impact initiatives that drive revenue growth and operational efficiency across Lifted. This role is not tied to a single function and is focused on building and launching new solutions. Projects can span any team, workflow, or problem where meaningful growth or efficiency can be created. You will operate without full information, make decisions decisively, and take full ownership of the outcomes (good and bad).

AI is a central lever in this role. You should be curious, pragmatic, and focused on applying it in ways that drive measurable business impact.

What You'll Do
  • Identify high-leverage opportunities across the business and build solutions to address them
  • Turn ambiguity into action by testing, iterating, and launching quickly
  • Move quickly with minimal guidance
  • Challenge assumptions and engage in hard debate
  • Build and ship solutions that create lasting impact
  • Do what it takes to win
  • Run experiments and adapt quickly based on results
  • Ensure every initiative leverages AI to improve how we operate and grow

This role is for you if:
  • You have built something from scratch (product, system, workflow, or business)
  • High say-do ratio
  • Comfort making decisions with
  • Tolerance for risk and direct feedback
  • Ability to hold multiple competing truths at once
  • Instinct to look for Option C when presented with A or B
  • Obsession with AI and its business applications

This role is not for you if:
  • You are more comfortable improving existing systems than building new ones from scratch
  • You prefer predictable environments
  • You have low risk tolerance
  • You require structured mentorship and defined playbooks
  • You avoid disagreement or difficult conversations
  • You are uncomfortable taking ownership of outcomes
  • You are unwilling to challenge assumptions, including those of the person you report to.

Lift Your Career. Shape the Future of Work.

We're proud to offer benefits that go beyond the basics, including comprehensive medical coverage for you and your family, unlimited PTO, a 401(k) plan with matching, and 12 weeks of paid parental leave.

The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.

Annual Base Compensation

$154,250-$254,250 USD

About Upwork

Upwork is a global freelancing platform where businesses and independent professionals connect and collaborate remotely. The company was founded in 2015 as a result of a merger between Elance and oDesk, two of the largest freelance marketplaces at the time. Upwork's platform allows businesses to find and hire freelancers for various projects, ranging from web development and design to writing and customer service. Freelancers can also use the platform to find work and build their careers. Upwork is headquartered in Mountain View, California and has offices in San Francisco, Chicago, and Oslo, Norway.
Learn more about Upwork
Size
650 employees
Market Cap
$1.2 billion
Industry
Net Income
-$22.8 million
Founded
1999
5 Year Trend
+25%
Revenue
$373.6 million
NASDAQ

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