Chief of Staff to the Enterprise GM

Upwork ($UPWK) is the world’s work marketplace. We serve everyone from one-person startups to over 30% of the Fortune 100 with a powerful, trust-driven platform that enables companies and talent to work together in new ways that unlock their potential.  

Last year, more than $3.3 billion of work was done through Upwork by skilled professionals who are gaining more control by finding work they are passionate about and innovating their careers.  

The Chief of Staff to the Enterprise GM will partner with the GM and their leadership team across Enterprise Sales, Operations, Solutions, Talent, Product, and Marketing. The CoS will build strong cross-functional partnerships both inside and outside the business unit and lead a portfolio of strategic long-range initiatives.

The CoS will be a strategic thought partner and provide a sounding board while sharing perspectives with the Enterprise GM, Enterprise leadership team, and Upwork executive team. Over time, the CoS will develop trust to become a proxy and force multiplier for the Enterprise GM, making decisions and driving prioritization of time and effort through their relationship as a trusted advisor.

Your Responsibilities:

• Manage strategic planning, budgeting processes, and executive communication preparation 

• Work with leaders to develop OKRs, ensure alignment & support measurement

• Lead a small team of Program Managers to provide oversight of business unit initiatives

• Manage rhythm and business unit cadences & align to company cadences 

• Maximize the time of the Enterprise leadership team and the Enterprise GM

• Drive feedback loops & strengthen integration across the business unit and organization

• Lead continuous improvement in processes, tools, & cadences

• Support & champion continuous operational improvement and exploration. Partner with leaders to build processes and structures that can scale with the company & business unit’s growth. 

• Incubation of new initiatives as appropriate and then spinning them off to other teams, or winding them down entirely and integrating our findings to future efforts.

• Advocating for all Enterprise priorities, from Product to Sales to Solutions to Talent, especially when their leaders are not in the room.

• Being a thought partner to the Enterprise GM

Requirements:

• Extensive knowledge of Enterprise Go-to-Market organizations.  

• Unquestionable ethics and integrity, a track record of impeccable judgment and doing the right thing even when nobody would know if you chose the easy alternative.

• Exceptional written and oral communication skills that enable preparation of both numeric and narrative driven keynotes, BoD work, all hands, presentations, memos for a range of audiences.

• Track record of cross-functional leadership & comfort partnering with Finance, Legal, HR, Marketing, Product, Engineering etc. to meet the organization’s needs.

• Outstanding financial acumen and understanding of short and long term implications of decisions to lead long range planning, budget creation and management, as well as ongoing resource allocation and projections.

• Consultative mindset to weigh the opportunities and costs of key investments

• Excellent program/project management skills with the ability to drive multiple complex strategic and operational initiatives simultaneously.

• Ability to think strategically from first principles while leading with a sense of urgency through ambiguities.

• Proven history of collaboration and positive cultural impact in a distributed team.

• Bias for action and a mentality that no job is too big or too small to be done the right way.

What it takes to catch our eye:

• Past experience in a similar role in B2B Enterprise organizations 

• 7+ years of experience in Enterprise consulting, Sales Leadership, or Business Operations

• Experience in structuring and executing complex analyses to support strategy in a fast-paced, continually evolving environment.

The annual base salary for this position in California and Washington ranges from $179,000 - $290,000. The range displayed reflects the minimum and maximum salary for this position in California and Washington, 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.

Come change how the world works.

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