Chief Operating Officer

Talantir; Northern (KY); Hybrid; USD 150,000 - 200,000; Full time

Benefits offered by this job

Equity participation

Remote work

Paid time off (3 weeks)

Professional development

Job summary

TechnologyMatch is actively transitioning from a high-touch services model to a scalable SaaS and AI-powered platform. You will drive disciplined execution across the organization, partnering with the CEO on strategic direction and platform growth.

This remote, full-time COO/Strategic Operator role requires a proven leader who can steer transformation, productize workflows, and elevate margins while maintaining culture and accountability.

Qualifications

• Proven experience scaling a SaaS or tech business.
• Experience driving transformation from services to software revenue.
• Strong financial Fluency with P&L and SaaS metrics.

Responsibilities

• Serve as the primary Integrator, owning operations so the CEO can focus on strategy and growth.
• Lead organizational design and platform-led operating model changes.
• Own operational P&L with CEO and CFO; drive ARR and margin expansion.

Skills

SaaS scaling experience

Cross-functional leadership

Financial fluency

AI tools familiarity

Change management

Tools

Salesforce

QuickBooks

CRM tools

Job description

WHO WE ARE

TechnologyMatch is a buyer-first B2B technology matchmaking platform transforming how enterprise IT leaders discover and evaluate technology partners.

We combine proprietary buyer intent data, intelligent automation, and human-led qualification to connect vetted enterprise technology vendors with verified demand. Unlike traditional demand generation models, we focus on alignment, intent, and fit — delivering high-trust introductions that accelerate real purchasing decisions.

Today, the majority of our revenue is driven by high-touch services. We are actively transitioning toward a unified AI-integrated platform where automation, SaaS subscriptions, and agentic systems drive scalable recurring revenue.

We are profitable, with established enterprise relationships and meaningful recurring revenue, and are now focused on materially increasing platform-driven ARR as a percentage of total revenue.

CORE VALUES

• We tell the truth with heart: We speak honestly and directly, We don’t avoid hard conversations, We give feedback with care and respect & We assume positive intent
• We are always evolving: We seek to learn and improve, We adapt when something isn’t working, We don’t cling to outdated ways & We take initiative to get better
• We own outcomes: We take responsibility for results, We don’t wait to be told, We don’t blame constraints & We fight for the outcome
• We execute with excellence: We do high-quality work, We finish what we start, We pay attention to details & We take pride in our craft

JOB DESCRIPTION

The Technology Match team is looking for a seasoned, commercially sharp COO/Strategic Operator with a proven track record in SaaS environments and business transformation. This is not a role for someone learning the ropes, we need someone who has navigated a business through a major evolution before and can do it again.

You’ll step into a pivotal moment: we are actively transitioning from a high-touch services model to a scalable SaaS and AI-powered platform. The CEO is driving strategic vision and platform direction. This role ensures disciplined execution across the organization.

The application code word is EMPOWER. This role requires a highly skilled strategic thinker who anticipates and solves problems in a self-directed way, and who empowers the team to move fast while maintaining quality and culture.

This is a full-time, remote position, and open to a W2 or 1099 agreement. Given the critical nature of this role, we host a rigorous, 4-part application process.

WHAT MAKES THIS ROLE UNIQUE

You are stepping into a profitable company at a strategic inflection point.

TechnologyMatch has strong market traction, established enterprise relationships, recurring revenue, and proprietary technology in development. The strategic direction is clear. The CEO is driving platform vision, AI strategy, and long-term capital positioning. What’s needed now is disciplined operational leadership to execute the transformation with rigor and measurable progress.

This is not a maintenance role. It is a structural evolution of the revenue engine.

THE TRANSFORMATION MANDATE

The business currently generates the majority of its revenue through high-touch services. The strategic objective is to transition toward a unified AI-integrated platform where automation, SaaS subscriptions, and agentic systems become the primary drivers of scalable recurring revenue and margin expansion.

Your mandate is to operationalize that shift.

This includes:

• Increasing platform-driven revenue mix as a percentage of total ARR while expanding gross margin
• Productizing repeatable service workflows into scalable platform functionality
• Reducing manual execution through AI-augmented and agentic automation
• Consolidating fragmented systems into a unified operating and reporting infrastructure
• Defining and executing a quarterly revenue mix shift plan tied to ARR and margin targets
• Aligning all operational decisions with an exit-oriented, high-multiple software trajectory

This is not a cosmetic SaaS overlay. It is a structural revenue model transformation.

Your success will be measured by tangible shifts in revenue composition, operational efficiency, margin profile, and founder independence from day-to-day execution.

RESPONSIBILITIES

Strategic Execution & Business Transformation

• Serve as the primary Integrator, assuming full operational ownership so the CEO can focus exclusively on strategy, capital, and growth.
• Lead organizational design and restructuring decisions required to support a platform-led operating model
• Own operational P&L accountability in partnership with the CEO and CFO
• Drive the deliberate reduction of services dependency by converting repeatable service workflows into scalable, AI-powered platform functionality that increases recurring revenue and margin.
• Ensure all business functions and decisions are aligned with the exit strategy and SaaS growth trajectory
• Hold the leadership team accountable to strategic priorities and quarterly OKRs/Rocks
• Establish guardrails for founder input to maintain strategic focus and operational consistency
• Define and execute a clear revenue mix shift plan with quarterly targets for platform-driven ARR
• Establish a quarterly scorecard that tracks revenue mix, margin expansion, platform adoption, and operational efficiency

Product & Technology Ownership

• Partner with the CTO to prioritize platform features that directly increase recurring revenue and margin expansion
• Define how AI and automation can be deployed to scale previously manual workflows
• Ensure all roads lead back to platform adoption and SaaS growth metrics (ARR, retention, NRR)

Operational & Process Management

• Build efficient, documented processes and procedures across all operational functions
• Establish a clear operating system for the business
• Redesign and optimize systems to remove bottlenecks and squeeze margin from existing infrastructure
• Oversee and develop the existing Operations Manager as your 2IC

Finance & Data Integrity

• Partner with the fractional CFO to ensure financial reporting is accurate, timely, and used for strategic decisions
• Rectify data integrity issues and establish a single source of truth across all reporting
• Manage financial planning and analysis to support the growth and exit timeline
• Track and report on SaaS-specific metrics including revenue mix, gross margin, CAC efficiency, retention, and NRR
• Build dashboards and reporting infrastructure that give leadership real-time operational visibility

People & Change Management

• Lead and manage cross-functional teams across services, product, and operations
• Own the change management process as the company transforms its business model
• Have the difficult conversations and drive accountability that the business needs to grow
• Build trust with a team navigating significant change, maintaining morale while raising standards

Success in this role means materially increasing platform-driven revenue mix, improving gross margin, and positioning the business for a high-multiple software valuation.

REQUIREMENTS

Non-Negotiable Experience

• Proven experience scaling a SaaS or technology business, including growing ARR and improving margins
• Experience working toward or preparing a company for acquisition or exit
• Track record navigating a business through a services-to-SaaS or business model transformation
• Experience as an Integrator or COO in a founder-led business, including managing up and extracting founders from day-to-day operations
• Familiarity with EOS (Entrepreneurial Operating System) methodology
• Experience managing cross-functional teams and driving accountability at a leadership level
• Strong financial fluency: P&L management, FP&A, SaaS financial metrics, and working with CFO-level partners
• Comfort working with AI tools, automation platforms, and modern SaaS tech stacks

Core Competencies

• Systems thinking: ability to see how services, technology, and people connect into a unified operating model
• Strategic planning and execution: reverse engineering a 2-3 year vision into 90-day priorities
• Data and reporting infrastructure: building dashboards and KPIs that enable real-time decisions
• Change management: guiding teams through business model evolution without losing momentum or morale
• Product translation: converting operational needs and service workflows into technology requirements

Critical Soft Skills (Deal-Breakers)

• Direct, decisive communicator who drives accountability without hesitation
• Comfortable with strong founder personalities and skilled at managing up constructively
• Able to create guardrails for visionary input without stifling creativity
• Resilient under pressure and comfortable leading through ambiguity and transformation
• High emotional intelligence to navigate team dynamics during periods of significant change
• Proactive problem-solver who identifies and addresses issues before they become fires

Technical & Logistical Requirements

• Must be available during US Eastern Time core collaboration hours
• Comfortable operating in a fully remote environment across distributed teams
• Proficient with project management tools, CRM systems (Salesforce preferred), and financial platforms (QuickBooks preferred)
• AI-literate and actively curious about how technology can augment and automate operations

BENEFITS

• Compensation bandwidth of $150,000 to $200,000 commensurate with experience
• Equity participation — open to discussion based on candidate profile and alignment
• 1099 Contractor or W2 relationship offering maximum autonomy in how you structure your work
• Time Off Policy - 3 Weeks for the first year in the organization.
• Standard US holidays observed throughout the calendar year.
• Professional Development: This role will be supported by an external Ops program that includes Ops mentorship, community, and live coaching.

Job Type: Full-time

Pay: $150,000.00 - $200,000.00 per year

Benefits: Paid time off

Professional development assistance

Work Location: Remote