When you are CEO of a $5M to $25M company, you don’t have one job. You have 15.
You can’t fix marketing without fixing messaging.
You can’t scale without process.
You can’t grow if everything revolves around you.
Sidekick isn’t an business consultant. It’s your one place for strategy and execution — across your business.
You don’t need a another business consultant. You need a Sidekick.
Don’t ask us. Ask one of the 600 CEOs we’ve helped.
When you are CEO of a $5M to $25M company, you don’t have one job. You have 15.
You can’t fix marketing without fixing messaging. You can’t scale without process. You can’t grow if everything revolves around you.
Sidekick isn’t an business consultant. It’s your one place for strategy and execution — across your business.
You don’t need a another business consultant. You need a Sidekick.
Don’t ask us. Ask the 600+ CEOs we’ve helped.
15 Critical Issues Every CEO Faces
At $5–25M, you’re not just leading — you’re solving 15 business-breaking challenges.
Competition
Cash Flow
Revenue Strategy
Sales Excellence
Marketing Excellence
Performance Management
Raising Money
Setting Goals
Financial Plan
Being a CEO
Scaling
No More Solar System
Setting Priorities
Legal Strategy
Time Management
Built by a CEO Who’s Lived It
Michael Dermer didn’t just build a company—he created an industry. He founded the first business in the U.S. to reward people for healthy behavior. What did they tell him – “No one will ever pay people to be healthy.” Sound familiar?
He scaled it to 800 employees and watched what he built for 10 years nearly get destroyed in 10 days in the 2008 financial crisis. He came back, sold the company, and is considered the pioneer of that iundustry. Now he helps CEOs solve the 15 issues that stall growth. Sidekick is strategy, execution, and judgment—from someone who’s sat in your seat.
We Know Your Challenges
You’ve got customers—but no scale
You’ve got revenue—but spotty growth
You’ve got payroll—not performance
You’ve got a team — you’re the bottleneck
You’re growing—but have no cash
It’s a family that doesn’t know business
You’re the CEO—but feel overwhelmed
It’s a SOLAR system and you are the sun.
How Packages Work
Your Sidekick helps you address these critical issues in a consulting package tailored to the number of hours and deliverables you need. Packages includes a number of hours, weekly check-ins, deliverables, and 1 year access to the Learning Community. Prices range from $5,000 to $50,000.
Sidekick Changes the Game for CEOs
Don’t ask us. Talk to the CEOs we’ve helped.
Our customers say, “I wish I found you a year earlier. It’s like 911 for CEOs.”
Every CEO needs a Sidekick — one place they turn to for strategy, guidance and execution.
Built by a CEO Who’s Lived It
Michael Dermer didn’t just build a company—he created an industry. He founded the first business in the U.S. to reward people for healthy behavior. What did they tell him – “No one will ever pay people to be healthy.” Sound familiar?
He scaled it to 800 employees and watched what he built for 10 years nearly get destroyed in 10 days in the 2008 financial crisis. He came back, sold the company, and is considered the pioneer of that iundustry. Now he helps CEOs solve the 15 issues that stall growth. Sidekick is strategy, execution, and judgment—from someone who’s sat in your seat.
Watch Michael’s Story
At Sidekick, we don’t consult — we deliver change across the 15 critical issues that make or break $5 to $25m companies. These are the issues we see over and over again in companies that are not achieving the success they deserve. And we don’t just know the issues — we know how to solve them. This is not theory. It’s execution. It’s accountability. It’s measurable business outcomes.
Beating the Competition
What Sidekick Delivers:
- Deep market and competitive assessment
- Define your unique “playground” and market space
- Form messaging that makes you the only logical choice
- Identify unfair advantages you can own
- Build a positioning roadmap to dominate niche segments
Success Metrics:
- Increased win rate vs competitors
- Higher % of inbound leads
- Positioning clarity in team and pitch
- Niche dominance measured by share
- Improved conversion from top-of-funnel
Cash Flow Optimization
What Sidekick Delivers:
- Detailed audit of current cash in/out flows
- Implement cash-conversion cycle improvement tools
- Introduce 13-week rolling cash forecasts
- Tailor pricing and billing to improve collections
- Build dashboards to monitor cash runway weekly
Success Metrics:
- Weekly 13-week cash model in place
- Reduced days sales outstanding (DSO)
- Increased gross and net cash flow margin
- Lower burn rate
- Fewer surprises in cash availability
Financial Plan
What Sidekick Delivers:
- Multi-year financial model tied to strategic goals
- Breakout model by revenue stream and margin center
- Budgeting tied to goal-driven initiatives
- Rolling reforecast to adjust for real-time changes
- System to monitor plan vs actual variances weekly
Success Metrics:
- Accurate monthly reporting and forecasts
- Plan vs. actual tracked in real-time
- Improved EBITDA margin
- Leadership financial fluency scores
- Clear unit economics per revenue stream
A True Revenue Strategy
What Sidekick Delivers:
- Map offers, pricing, channels, and ICP together
- Diagnose leaks and friction in buyer journey
- Develop segmentation and positioning
- Align revenue plan to operations and finance
- Create forecast models and tracking
Success Metrics:
- Revenue growth and predictability
- Forecast vs actual accuracy
- Customer acquisition cost ↓
- Segment profitability clarity
- Improved conversion at each stage
Sales Excellence
What Sidekick Delivers:
- Audit of full sales funnel and CRM
- Clarify Ideal Customer Profile (ICP)
- Build and install sales playbook
- Training on objection handling and closing
- Weekly pipeline review cadence
Success Metrics:
- Improved close rate
- Shorter sales cycles
- Deal size growth
- Pipeline stage clarity
- Playbook adoption %
Marketing Excellence
What Sidekick Delivers:
- Audit current marketing channels and spend
- Clarify messaging and positioning
- Install calendar and cadence for campaigns
- Assess CAC by channel and ROI
- Integrate marketing with sales flow
Success Metrics:
- Improved CAC:LTV ratio
- Lead quality and conversion ↑
- Campaign ROI by channel
- Consistent campaign rhythm
- Clear funnel attribution
Performance Management
What Sidekick Delivers:
- Establish metrics for each role and team
- Create a performance-review rhythm with scorecards
- Diagnose team capacity and productivity gaps
- Coach leaders to manage outcomes, not tasks
- Integrate people + process + metrics into one system
Success Metrics:
- % of team with clear KPIs
- Employee performance tiered by outcome
- % of goals hit quarterly
- Manager leadership score improvement
- Reduced people-related execution gaps
Raising Money
What Sidekick Delivers:
- Investment-ready financial model and projections
- Investor storytelling aligned with your differentiators
- Coaching for founder pitch style and Q&A prep
- Decks and documents tailored to relevant investor types
- Roadmap for timing / process of due diligence and close
Success Metrics:
- Investor meetings booked
- Investor close %
- Deck quality and completeness
- Financial model accuracy and clarity
- Founder confidence and pitch readiness
Setting Goals
What Sidekick Delivers:
- Company-wide goal cascades tied to revenue and margin
- Departmental / functional targets aligned to strategy
- Link goals to cash, performance, and growth metrics
- Goal-tracking dashboard in real time
- Weekly review process to drive accountability
Success Metrics:
- % of org aligned to company goals
- Goal completion % by quarter
- Cross-team alignment score
- Reduction in reactive vs strategic activity
- Goals linked to revenue/profit targets
Being a CEO
What Sidekick Delivers:
- Define CEO vs. founder role and focus areas
- Build personal leadership priorities roadmap
- Coaching structure for decision-making clarity
- System to offload non-CEO work to team
- CEO scorecard tied to business outcomes
Success Metrics:
- Time spent by CEO on highest-leverage tasks
- Reduction in reactive firefighting
- CEO confidence/self-reporting
- Team clarity on CEO vs. ops roles
- CEO involvement in strategic vs. tactical issues
Scaling
What Sidekick Delivers:
- Organizational structure to support scalable growth
- SOPs for operations, marketing, onboarding
- Repeatable processes to reduce chaos
- Capacity planning to support expansion
- Scorecards to manage scale
Success Metrics:
- Team scale readiness
- SOP completion and adoption
- Time-to-onboard reduced
- More with less: output-to-headcount ratio
- Revenue per employee growth
No More Solar System
What Sidekick Delivers:
- Remove the CEO as bottleneck
- Decision rights by role
- Escalation paths and clarity
- Train managers to manage
- Install rhythms for autonomy
Success Metrics:
- CEO time reclaimed
- Decisions made w/o CEO
- Leadership effectiveness scores
- Manager accountability benchmarks
- Culture of ownership
Setting Priorities
What Sidekick Delivers:
- Quarterly “Big Rocks” system
- Weekly progress reviews
- Define what matters most
- Remove distractions
- Scorecard tie-in for visibility
Success Metrics:
- % of time aligned to strategy
- Top 5 priorities clearly tracked
- Completion % of Big Rocks
- Project traffic light reporting
- Team clarity on priorities
Legal Strategy
What Sidekick Delivers:
- IP, contract, compliance coverage
- Legal risk audit across business units
- Standard templates and contract process
- Contract renewal calendar and tracking
- Oversight protocols for ongoing legal needs
Success Metrics:
- Risk item resolution %
- Legal template library completeness
- Fewer missed contract renewals
- Faster contract execution time
- IP security and clarity
Time Management
What Sidekick Delivers:
- CEO time audit and time-blocking structure
- Weekly “What Matters Most” rhythm
- Deep work and strategy time protocols
- Delegation frameworks by role
- Productivity rituals and tracking
Success Metrics:
- % time spent on strategic work
- Delegation success rate
- Meeting time % reduced
- CEO time reclaimed
- Calendar alignment to priorities