Chief of Staff

Sonatafy Technology is a Software Delivery Acceleration Systems company headquartered in Scottsdale, Arizona. We help organizations accelerate software delivery through a combination of strategic consulting and Managed Delivery PODs, where US-based Principal Engineers lead senior LATAM engineering teams operating in US time zones with full backlog ownership.

We have completed 60+ client engagements, earned 3x recognition on the Inc. 5000, and achieved 408% revenue growth over 3 years.

Our founder and CEO is a serial entrepreneur who has launched 30+ companies over 25+ years, is a Forbes Technology Council member with 248+ published articles, is a host of the Software Leaders Uncensored podcast (195+ episodes), and is the author of two published books with three more currently in development.

Sonatafy operates at the intersection of enterprise technology consulting, software delivery execution, AI and technical strategy, thought leadership and media, and growth stage GTM expansion. This role sits at the center of it all.

The Role

This is not a traditional administrative or project management position.

The Chief of Staff to the CEO is an execution and operating systems role designed to create leverage for the CEO and alignment across the organization. You will serve as the connective tissue between strategic priorities and operational execution across sales, marketing, delivery, technical strategy, and brand. You will build and manage the business's operating cadence, drive accountability through systems and structure, coordinate cross-functional execution, and ensure strategic initiatives move forward without constant CEO intervention.

You will report directly to the CEO and work alongside a leadership team that includes a CTO, VP of Marketing, VP of Operations and Account Management, Director of Technical Strategy and Growth, Principal Data and AI Architect, and fractional and outsourced partners in GTM strategy and outbound sales development.

This role is ideal for someone who thrives in fast-moving, founder-led environments and enjoys bringing clarity, structure, and accountability to complex organizations with multiple concurrent workstreams.

What You Will Own

Operating Cadence and Accountability Systems

Build and run the weekly, biweekly, monthly, and quarterly operating rhythm across the leadership team. Design and maintain dashboards, trackers, reporting structures, and workflows within ClickUp and HubSpot that create visibility into priorities, deliverables, deadlines, ownership, and execution risk. You are the person who ensures commitments are visible, tracked, followed up on, and completed.

Cross-Functional Coordination

Ensure alignment between marketing strategy and daily execution; GTM planning and outbound sales activity; delivery operations and account management; AI practice development and technical initiatives; and leadership priorities and operational follow-through. Multiple initiatives move simultaneously across the company. You ensure they stay synchronized.

Meeting Design and Facilitation

Own the structure and facilitation of leadership meetings, cross-functional syncs, and operational reviews. Every meeting should produce decisions, accountability, documented next steps with owners, and deadlines. You will independently facilitate operational meetings and escalate only decisions that require CEO involvement.

Strategic Project Management

Drive high-priority initiatives from planning through execution. Examples may include enterprise proposal coordination, multi-channel GTM launches, operational process rollouts, AI initiative coordination, website and digital property launches, research and partnership projects, and cross-functional execution initiatives. You turn strategic priorities into executed outcomes.

Fractional and Outsourced Partner Management

Coordinate day-to-day execution with fractional and outsourced partners operating alongside internal leadership. Ensure deliverables are clearly defined, timelines are visible, accountability is established, and communication loops remain closed. The CEO should not need to personally manage every operational interaction.

CEO Leverage and Decision Support

Prepare briefing materials, synthesize operational and pipeline data, identify blockers before they escalate, and create visibility into the health of organizational execution. Your role is to protect the CEO's time for the highest leverage activities: client relationships, strategic direction, partnerships, thought leadership, and growth initiatives.

What Success Looks Like After 12 Months

The leadership operating cadence runs predictably with minimal CEO intervention. Cross-functional initiatives execute with clearer accountability and faster follow-through. ClickUp and HubSpot become trusted operational systems across departments. Leadership meetings consistently drive decisions and outcomes. Strategic initiatives move from concept to execution faster and with fewer bottlenecks. Fractional and outsourced partners operate with greater alignment and visibility. The CEO spends substantially less time on tactical coordination and follow-up.

What We Are Looking For

Systems Thinker Who Executes

You do not just design processes. You operationalize them. You build systems inside tools, drive adoption, measure effectiveness, and continuously improve execution. You are the kind of person who builds a ClickUp workflow on Monday and is already tracking adoption metrics by Friday.

Operational Accountability Mindset

You hold teams accountable through visibility, structure, documented ownership, operating cadence, and systems, not through escalation or micromanagement. When deadlines slip, you already know because the system surfaced it, and you already have a plan to get it back on track.

ClickUp, HubSpot, and Automation Proficiency

Deep working knowledge of ClickUp, including spaces, folders, lists, automations, dashboards, custom fields, and workflows. Working proficiency in HubSpot CRM, including pipeline visibility, reporting, activity tracking, and deal stage management. You do not need to be a HubSpot admin, but you need to pull reports, understand deal stages, and connect sales activity to outcomes. Experience with n8n or similar workflow automation platforms is also preferred. We use n8n to connect systems, automate operational handoffs, and reduce manual coordination across tools, and a candidate who can build or manage these automations adds immediate value.

EOS Experience Strongly Preferred

Experience working within EOS (Entrepreneurial Operating System) environments is a significant plus. Ideal candidates understand concepts such as Rocks, Scorecards, Accountability Charts, L10 meetings, quarterly planning, cascading priorities, and operational cadence management. Experience serving as an operational integrator or supporting founder-led EOS organizations is highly valued.

Communication and Judgment

You can represent the CEO professionally with internal leaders, clients, and external partners. You know when to decide, when to escalate, when to gather more information, and when to push for accountability. You communicate directly, clearly, and without ambiguity.

Comfort With Complexity

Sonatafy operates across enterprise sales, software delivery, AI strategy, media and thought leadership, and vertical market expansion simultaneously. You are energized by managing multiple interconnected workstreams, not overwhelmed by them.

Qualifications

• 5+ years in a Chief of Staff, operations, program management, or senior project management role, ideally in a technology services, SaaS, consulting, agency, or professional services environment.
• Demonstrated success building and running operating cadences within founder-led organizations, including daily and weekly syncs, OKR tracking, and quarterly planning cycles.
• Advanced proficiency with ClickUp (or equivalent platforms such as Asana or Monday with a willingness to adopt ClickUp. Working proficiency in HubSpot CRM. Experience with n8n or similar workflow automation tools preferred.
• Experience coordinating distributed, outsourced, or fractional team members alongside full-time staff.
• Strong written and verbal communication skills. You can draft a client email, prepare a board briefing, or write a meeting recap with equal fluency.
• Phoenix metro-based, with the ability to work in person regularly with the CEO and leadership team in Scottsdale.

How to Apply

Send your resume along with a brief note (one page maximum) explaining how you have built operational accountability systems, how you have driven cross-functional execution, and what tools and frameworks you used to keep teams aligned and accountable.

We care far more about operational thinking, execution capability, and systems leadership than we do about traditional credentials.