Operators, not observers
Compare notes with people carrying the same hat
A private peer community for operators carrying an executive function without the full-time title. General C*O conversation first, then the topics that matter to each function. Signed-in members read and reply free; plans and trials start threads.
- topics
- 36
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- 360
General C*O Discussion
Cross-functional conversation for everyone carrying an executive hat without the full-time title.
Introductions
Who you are, what you run, and which hat you're wearing this quarter.
General Discussion
Running the business, the market, the week; anything cross-functional.
Fractional & Part-Time Exec Life
Scoping engagements, juggling clients, pricing your time, and saying no.
Hiring Your First Executive
Full-time vs fractional vs agency vs AI tooling, comp, expectations, first 90 days.
Tools & Stack
What's actually working in the operating stack and what got ripped out.
Wins & Lessons
What worked, what didn't, and what you'd do differently.
CFO · Finance
Cash, capital, close and the numbers the board asks about.
Cash Flow & Runway
13-week cash forecasts, collections, DSO, seasonality, and lines of credit for lean teams.
Fundraising & Capital
Debt vs equity, SBA and term loans, revenue-based financing, investor updates, and PE dynamics.
Budgeting & Forecasting
Annual plans, rolling forecasts, driver-based models, and what to do when the plan breaks.
Close, Accounting & Tax
Month-end close, bookkeeper and CPA relationships, revenue recognition, sales tax, and R&D credits.
Pricing & Unit Economics
Margins, price increases, packaging, CAC payback, and gross margin by segment or location.
Finance Stack & Automation
Accounting and ERP systems, spend management, AP/AR automation, and what to automate first.
CMO · Marketing
Positioning, demand, content and proving what marketing actually moved.
Brand & Positioning
Positioning statements, category choice, messaging hierarchy, and rebrand timing.
Content & SEO
Content programs, search, AI answer engines, editorial cadence, and what converts.
Demand Gen & Paid Media
Paid search and social, budget allocation, CAC, agency vs in-house, and local ads.
Analytics & Attribution
Dashboards, attribution honesty, pipeline sourcing, and reporting to the CEO or board.
Product Marketing & Launches
Launch plans, sales enablement, pricing pages, and customer proof.
Martech Stack & Automation
Email, CRM, and automation tooling, consolidation, what to rip out, and AI in the workflow.
CRO · Revenue
Pipeline, process, comp and keeping the customers you already won.
Pipeline & Forecasting
Stage definitions, coverage ratios, forecast calls, commit vs best case, and honesty with the board.
Sales Process & Methodology
Discovery, qualification, demos, proposals, deal reviews, and moving from founder-led to rep-led selling.
Compensation & Quotas
Plan design, OTE splits, quota setting, accelerators, and SDR, AE, and CS compensation structures.
Outbound & Prospecting
Sequences, lists, deliverability, SDR vs AE-led outbound, and what's actually still working.
Customer Success & Retention
Onboarding, renewals, churn signals, expansion, QBRs, and who actually owns the renewal.
RevOps & CRM
CRM hygiene, pipeline reporting, lead routing, sales-marketing handoff, and tooling consolidation.
COO · Operations
Cadence, process, people and the systems that make the week run.
Operating Cadence & Meetings
Weekly and quarterly rhythm, scorecards, decision logs, and killing meetings that decide nothing.
SOPs & Process Design
Documenting how work actually gets done, checklists, handoffs, process debt, and when to standardize.
People Ops & Hiring
Hiring plans, onboarding, performance conversations, managers of managers, and retention.
Vendors & Procurement
Vendor selection, contract renewals, consolidating spend, and outsourcing versus in-house.
Systems & Automation
Workflow tooling, integrations, AI in operations, what to automate first, and failed automations.
Metrics & Dashboards
Choosing the few numbers that matter, dashboard sprawl, leading versus lagging, reporting to owners.
CTO · Technology
Architecture, security, vendors and getting real value out of AI.
Architecture & Tech Debt
When to rewrite vs refactor, inherited codebases, agency handoffs, and paying down debt without stopping the roadmap.
Security & Compliance
SOC 2 and deal questionnaires, access control, backups, incident basics, and insurance asks, no legal advice.
Engineering Team & Hiring
First engineering hires, contractors vs employees, offshore teams, and managing without being technical.
Build vs. Buy & Vendors
SaaS sprawl, integrations, vendor lock-in, contract terms, and when it's actually worth building.
AI & Automation
Where AI actually helped or didn't, governance, data hygiene, coding assistants, and agent experiments.
Cloud Cost & Infrastructure
Hosting bills, reserved vs on-demand, observability, and reliability on a small team.
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