Chief Operating Officer

Bristlecone Companies

Chief Operating Officer at Systrends managing operational foundation for regulatory compliance software. Overseeing planning, reporting, vendor relationships, and organizational structure in a remote work setting.

Posted 7/27/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

Align on and implement an operating framework, establishing a consistent rhythm of goal setting, reporting cycles, and cross-functional accountability that runs without single-person dependency
Drive quarterly and annual planning, translating growth objectives into clear priorities, grounded resource plans, and realistic investment figures
Own the financial operating picture: partner with Finance on reporting, drive the operational data infrastructure, and ensure the ELT is making decisions from shared, accurate numbers
Define the org structure intentionally, identify gaps, and fill them with quality people; partner with CEO across talent recruiting, onboarding, development, engagement, and retention
Set a high bar and build an environment where communication flows, ownership is clear, and the whole team is pulling in the same direction
Architect how the business operates procedurally and own the implementation — CRM configuration, CS workflows, GTM tooling, onboarding processes, and more
Own commercial relationships with vendors, ensuring material contracts, compliance obligations, and operational risks have a clear owner and are managed proactively
Be a thought partner to the CEO on growth and help design and build more robust engines for customer acquisition, expansion, and retention

Requirements

What you’ll need

Operating experience in a $2-10M ARR SaaS business on an upward career trajectory
Experience building operating infrastructure in high-change environments (high-growth, post-acquisition, founder-led, or operationally complex businesses)
High agency and ownership mentality: bias for action, operates well in ambiguity, and takes responsibility for outcomes
People management experience with a track record of earning genuine followership while holding a high performance bar
Strong financial acumen: comfortable reading a P&L, partnering on a budget, and translating growth objectives into grounded operating plans
Execution-oriented and hands-on: personally builds systems, fixes operational gaps, and owns implementation alongside strategy
Exceptionally organized with high personal standards for follow-through and detail
Clear, precise written and verbal communicator who adapts to audience
Highly proficient, experimental, and genuinely ahead of the curve in deploying AI and modern tooling into core workflows to build more with less

Benefits

Comp & perks

Competitive base salary
Performance-based bonus
Equity participation
Periodic travel required for team offsites and client events