Corporate Wellness Program

The shortcut: Stop selling wellness to employees. Sell it to the HR director who has a 4 PM board meeting on Thursday and needs to walk in with a number for "what we're doing about absenteeism." That meeting is the entire sales cycle in one sentence.

Industry: Fitness & Sports Investment level: Small — $3,000-$10,000 Time to launch: 10-16 weeks (the wellness coach cert is fast; landing the first paid HR contract is the long pole — expect 8-12 weeks of pipeline before the first signed proposal) Best for: Someone with a fitness or health-coaching background who can sit across a conference table from a benefits manager and talk through a one-page proposal without flinching at the words "PEPM," "ERISA," or "engagement rate." What you'll likely make: month 3 $0-$1,500, month 6 $2,500-$5,500, month 12 $6,000-$11,000. Math is in Section 4.

Market Opportunity

The HR director who buys your program has never used it personally and probably never will. She is buying a story she can tell her CFO at the next budget review — that the company spent $18,000 last year on a wellness vendor and absenteeism dropped 6%. Hand her that story in a one-page proposal and you win the contract. Talk about chakras or "engaging the whole employee" and you lose to Wellable in the first ten minutes.

The U.S. corporate wellness market sits around $51 billion in 2023, projected near $100 billion by 2030. About 80% of companies with 50+ employees already offer some form of wellness benefit, but only around 23% of employees actively participate. The gap between "we have a program" and "people use it" is the entire opening for a small independent. Big platforms like Personify Health (formerly Virgin Pulse) win the Fortune 500 deal. Nobody is fighting hard for the 75-person accounting firm that just had two senior partners go out on stress leave.

At companies under 200 people, the buyer often isn't HR at all — it's the COO, the head of people ops, or the founder's chief of staff. Title matters less than the pain. Find the person who got yelled at last quarter about retention or healthcare premium hikes, and you have your meeting.

Launch With AI

Pro tip: The HR-director-board-meeting framing is the entire sales cycle. AI handles the per-vertical HR-buyer cold pitch (the 'absenteeism dropped 6%' narrative), the GINA + HIPAA + ERISA wellness-rules compliance (do NOT collect biometric data without legal counsel — GINA fines start at $100/day per affected individual), the engagement-rate dashboard that proves ROI to the CFO, and the kickstart-challenge → quarterly-retainer conversion flow.

Upfront honesty: AI cannot deliver a Tuesday lunch-and-learn that gets 30% participation in a 200-person company. The room-leadership + behavior-change craft is your moat. What AI does is everything around it: HR-buyer cold pitches that frame absenteeism + premium-cost stories (the language CFOs sign-off on), GINA + HIPAA + ERISA Wellness Program rule compliance (29 CFR §2590.702-1 + §2590.702-3 — get this wrong + your $30K contract triggers a $50K-$500K DOL/EEOC fine), scope-safe positioning that keeps you OUT of clinical-medical (no biometric screenings, no individualized nutrition plans without an RD on staff, no mental-health counseling without licensed therapist), engagement-rate dashboard generation, and the Klaviyo flow that turns one $1,500 kickstart into a $36K annual retainer in 12 months.

AI Tools You'll Use

Tool	What it does for you	Cost
ChatGPT (Plus)	HR-buyer cold pitches, scope-safe positioning, engagement-rate dashboards	$20/mo
Claude (Free)	Reading GINA + HIPAA + ERISA wellness rules + state-specific privacy laws	Free
YuMuuv or simple Google Sheet	Steps/hydration/movement challenge engagement tracking	$1-$3/employee/mo
Typeform + HelloSign + Stripe	Pre-program baseline survey + MSA signing + retainer billing	$25-$50/mo
Klaviyo (Free → paid)	Kickstart → quarterly retainer → annual PEPM conversion flow	Free → $20/mo

The Workflow

Step 1: Generate HR-buyer cold pitch with the absenteeism + premium-cost narrative. Most wellness coaches pitch employees. AI writes the pitch that gets the HR director's CFO sign-off.

Prompt: "Write a 4-line cold email + LinkedIn InMail I send to [HR director / VP of People / chief of staff] at [target mid-market company in my zip — 50-300 employees]. Hook: 'You probably had the same Q4 board meeting most HR leaders had — 'what are we doing about absenteeism + premium hikes' — and walked out with 6 vendor RFPs.' Bridge: 'Most of those vendors are platforms (Wellable, Personify Health) charging $15-$50 PEPM. They're great for the Fortune 500. For your tier (50-300 employees), the math doesn't work + the engagement is brutal because there's no human delivering the program.' Pitch: 'I run a 4-week kickstart challenge at $1,500-$2,500 fixed-fee — steps + hydration + 2 live virtual sessions + weekly engagement reports HR can take to your CFO. If it works, we move to a $1,500-$3,000/mo quarterly retainer. If it doesn't, you're out the kickstart fee + you have engagement data showing what your team will + won't show up for.' Sign with first name + cell + my NASM CWC or ACE Health Coach credential + my Calendly link. Tone: peer-to-HR-buyer, never sales-y. Avoid 'engaging the whole employee' or 'chakras' (the immediate disqualifiers in HR conversations)."

Step 2: Generate GINA + HIPAA + ERISA wellness-rules compliance audit. Wellness programs that collect biometric data trigger GINA (Genetic Information Nondiscrimination Act), HIPAA, AND ERISA wellness-program rules (29 CFR §2590.702-1 + §2590.702-3). Get this wrong = $50K-$500K fines + lawsuits. AI generates the compliance audit.

Prompt: "Generate a GINA + HIPAA + ERISA wellness-program compliance audit for my corporate wellness practice. (1) GINA SCOPE — applies to any wellness program that collects 'genetic information' (broadly defined: family medical history, individual genetic test results, etc.). FINES: $100-$500/day per affected individual. AVOIDANCE: do NOT collect biometric data (BP, BMI, cholesterol, A1C) in year 1 unless I partner with a licensed clinical vendor (NOT my LLC); do NOT ask family medical history; do NOT request genetic test results from employees. (2) HIPAA SCOPE — applies to any 'covered entity' or 'business associate' handling protected health information (PHI). My wellness program = NOT a covered entity if I'm working WITH the employer's existing health plan; I AM a 'business associate' if the employer's plan shares PHI with me. AVOIDANCE: do NOT receive PHI from employer's health plan; if PHI exchange is necessary, sign a HIPAA Business Associate Agreement (BAA) BEFORE any data flows + implement HIPAA Security Rule safeguards (encryption, access controls, breach notification within 60 days). (3) ERISA WELLNESS PROGRAM RULES per 29 CFR §2590.702-1 (participatory wellness programs — no health-status-based reward) + §2590.702-3 (health-contingent wellness programs — reward based on outcome, MAX 30% of premium-cost reduction = the limit on incentives, MUST offer reasonable alternative, MUST be reasonably designed to promote health). My 4-week kickstart = participatory program (everyone gets the same content + completion-based reward) → SAFE. Avoid: any program where reward is based on hitting biometric target (BP <140/90, BMI <30) — that's health-contingent + triggers all the rules. (4) ADA + EEOC RULES — wellness program participation must be 'voluntary' per EEOC's 2016 Final Rule (currently in regulatory limbo post-2018 vacatur — but conservative compliance = treat as voluntary, no penalty for non-participation, max 30% incentive). (5) STATE-SPECIFIC RULES — California's CCPA + Colorado's CPA + similar state privacy laws require disclosure + opt-out for any 'personal information' collected in wellness programs. (6) MY COMPLIANCE WORKFLOW — privacy notice at program start (what I collect + what I don't + how it's used + retention period); informed consent (opt-in checkbox, not pre-checked); data minimization (collect ONLY what's needed for engagement-rate reporting; NO individual-level health data); aggregated reporting only (HR sees 'team A has 65% participation' NOT 'employee X has BP 145/95'); no PHI handling (refer to existing health plan + EAP for clinical concerns). Output: per-rule compliance checklist + my client-facing privacy notice template + the BAA template if needed."

Step 3: Generate scope-safe positioning that keeps you OUT of clinical-medical territory. Without an RD (Registered Dietitian) credential or licensed-therapist credential, recommending individualized nutrition plans or providing mental-health counseling = unauthorized practice of nutrition or unauthorized practice of psychology = state professional-board complaint + criminal exposure. AI keeps you scope-safe.

Prompt: "I'm a NASM Certified Wellness Coach (or ACE Health Coach), NOT a Registered Dietitian (CDR), NOT a licensed therapist, NOT a medical provider. Read my draft proposal + program-content + sales-page copy below: '[paste].' Apply scope-of-practice red-team: (1) NUTRITION SCOPE — flag any sentence that prescribes specific calories/macros/individualized meal plans (these require RD credential per state nutrition-licensure laws); allowed: USDA Dietary Guidelines education, hydration education, food-as-fuel concepts, suggestions to 'consult an RD for personalized plans.' (2) MENTAL-HEALTH SCOPE — flag any sentence that diagnoses or treats anxiety/depression/burnout/stress disorders (these require licensed therapist or psychologist); allowed: stress-management education, breathing techniques, mindfulness practice, suggestions to 'consult your EAP or licensed therapist for clinical concerns.' (3) MEDICAL SCOPE — flag any sentence that diagnoses or treats medical conditions (allowed: NEVER); medications/supplements/dosages (allowed: NEVER without licensed provider); biometric interpretation (allowed: NEVER without clinical provider). (4) CHAKRAS + ENERGY HEALING + PSEUDOSCIENCE — flag anything that would torpedo my HR-buyer credibility or lead to refund demands. (5) BIOMETRIC SCREENINGS — flag if my proposal includes biometric screenings without clinical-vendor partnership (this triggers GINA/HIPAA + my insurance won't cover). For each flag: tell me the exact phrase, the legal/credibility risk, and rewrite in scope-safe language. Then generate the safe-language vocabulary list — preferred verbs ('explore,' 'discuss,' 'practice,' 'learn'), banned verbs ('treat,' 'cure,' 'diagnose,' 'fix,' 'individualize'). Add a footer disclaimer: 'I am a NASM Certified Wellness Coach. I am not a medical provider, registered dietitian, or licensed therapist. My services are educational + behavioral-change coaching. They are not a substitute for medical, nutritional, or mental-health care. Consult your physician, registered dietitian, or licensed therapist for personalized clinical guidance.'"

Step 4: Generate engagement-rate dashboard + monthly executive report (the data that wins the next contract). Most wellness vendors deliver smile-sheet feedback. AI generates the per-program dashboard that proves ROI to the CFO + locks renewal.

Prompt: "For each wellness engagement, generate a monthly executive report dashboard for the HR director to take to her CFO. Sections: (1) PROGRAM PARTICIPATION — # employees enrolled / # employees company-wide = participation rate (HEALTHY: 30-50%; CONCERNING: <20%; if my program hits >40% I'm doing something right). (2) ENGAGEMENT METRICS (per challenge / session / activity) — # actions completed (steps, hydration check-ins, session attendance), # employees engaged 50%+ of program duration, # employees engaged 80%+ of program duration. (3) BEHAVIOR-INDICATOR METRICS (NOT health metrics, since I don't collect biometric) — self-reported sleep quality (1-5 scale survey), self-reported energy at work (1-5), self-reported stress level (1-5) at week 1 + week 4. (4) HR-RELEVANT BUSINESS METRICS — partnered with HR's data: change in absenteeism rate during program window vs prior-quarter baseline; change in EAP utilization (often increases as awareness rises); change in leave requests (early indicator of burnout reduction). (5) THE EXECUTIVE NARRATIVE — 1-paragraph summary the HR director can paste into her board memo: 'Our 4-week kickstart had X% participation, Y% completed full program, employee-reported stress dropped from 4.2 to 3.1 on 1-5 scale, absenteeism rate decreased X% vs prior quarter. Engagement data supports continuing to a quarterly retainer at $1,500/mo.' (6) THE NEXT-PROGRAM RECOMMENDATION — based on what worked + didn't, recommend the next 90-day program scope (this is what wins the renewal). Output: the per-engagement dashboard template (Google Sheet or Airtable) + the monthly executive report template + the participation-rate optimization tactics if engagement <30%."

Step 5: Klaviyo kickstart → quarterly retainer → annual PEPM conversion flow. A successful $1,500 kickstart should become a $1,500/mo retainer in 60 days + a $30K annual PEPM in 12 months. AI writes the conversion flow.

Prompt: "Write a 4-email Klaviyo flow triggered after I deliver a successful 4-week kickstart program (sent to the HR-director buyer, NOT employees). Email 1 (1 day after final week): warm thank-you + the executive report dashboard PDF + the 'engagement metrics' summary the HR director can take to her CFO. Email 2 (14 days after): the quarterly retainer pitch — '60% of behavior changes from a 4-week program fade without ongoing reinforcement. The quarterly retainer at $1,500-$3,000/mo includes 2 weekly sessions + a private wellness Slack channel I moderate + monthly executive reports. Locks in the engagement we just built + adds the quarterly cycle that compounds.' + 1-paragraph case study of a similar company that went from kickstart → retainer → annual PEPM. Email 3 (45 days): the annual PEPM pitch — 'Once you have 60+ employees + we've delivered a quarterly retainer for 90+ days, the math typically shifts to PEPM ($15-$30 per employee per month) which gives you predictable annual budgeting + me dedicated capacity for your team. $30K-$80K annual depending on headcount.' Email 4 (90 days): the renewal-decision check-in + offer of a 30-min Q[N] strategy call to scope the next 6 months. Subject lines under 40 chars. Tone: peer-to-HR-buyer + business-outcomes-focused. Sign every email from my first name + my credential."

Time Saved Per Week

HR-buyer cold pitch (5 prospects/wk): ~3 hrs saved per outreach batch
GINA + HIPAA + ERISA compliance audit (one-time): ~10 hrs saved + $50K-$500K fine protection
Scope-safe positioning red-team (one-time): ~4 hrs saved + state-licensure-board protection
Engagement-rate dashboard per engagement: ~6 hrs saved per engagement + retainer-renewal protection
Klaviyo conversion flow (one-time): ~6 hrs saved, then runs forever
Total: 6-10 hrs/wk back in steady state — enough to add 1-2 more retainer clients per quarter without burning out.

Total AI Stack Cost

Budget tier: ChatGPT Free + Claude Free + Typeform Free + Klaviyo Free = $0/mo to start
Full tier: ChatGPT Plus ($20) + Typeform ($25) + YuMuuv ($1-3/employee) + Klaviyo ($20) = $65/mo + per-employee
Compare: A part-time admin doing scheduling + reporting + email = $400-$800/mo. AI does it for $0-$65.

Your First Win (30-min action)

Pick the closest 5 mid-market companies (50-300 employees) in your zip. Find the HR director / VP of People for each via LinkedIn. Use Step 1's prompt to write personalized cold emails today.

Prompt to write your moms-of-execs warm-intro pitch: "Write a 4-line warm-intro pitch I send to friends/family/network asking for HR-director introductions. Hook: 'I just launched a corporate wellness practice — looking for warm intros to HR directors at companies with 50-300 employees.' Bridge: 'Specifically: I'm targeting CFO-friendly absenteeism + premium-cost narrative, not the 'engage the whole employee' wellness fluff that HR is tired of. My 4-week kickstart at $1,500-$2,500 lets HR test me without procurement red tape.' Ask: 'If you know any HR director, VP of People, or chief of staff at a 50-300-person company, would you forward my [LinkedIn / 1-line about] for a 15-min intro call? I'll send a $50 thank-you for any intro that becomes a paid kickstart.' Sign with name + cell. Tone: warm + direct + never desperate. Send to 30+ contacts."

That single 5-cold + 30-warm-intro batch typically lands 2-3 HR-buyer conversations within 30 days. From those, 1 typically converts to a $1,500-$2,500 kickstart within 60 days. That's the entire 'first $0-$1,500 month 3' + 'first $2,500/mo retainer by month 6' path.

Product / Service Offering

Three things only. Don't build a 14-pillar wellness platform — you'll spend a year making slide decks and zero months collecting checks.

The 4-week kickstart challenge. $1,500-$2,500 flat fee. Steps or hydration challenge through YuMuuv or a Google Sheet leaderboard, two 30-minute live virtual sessions, weekly email recap. The foot-in-the-door product. HR can buy it on a corporate card without procurement review.
The quarterly program retainer. $1,500-$3,000/month. Two on-site or virtual sessions per week (movement, stress, sleep, nutrition basics), a private wellness Slack channel you moderate, monthly engagement report. Three- to six-month contracts with auto-renew language. The bread and butter.
Fully managed PEPM (per-employee per-month). $15-$50 per employee per month, 12-month minimum. Adds biometric screening coordination, a custom challenge calendar, and quarterly executive briefings. Don't pitch this until the company has 60+ employees and you've already delivered a kickstart or retainer with them. Wellable's PEPM model is the mid-tier market anchor.

A few things to deliberately exclude in year one. Skip biometric screenings (BP, BMI, cholesterol) unless you partner with a clinical vendor. The moment you collect that data you trip GINA and the legal layer triples. Skip mental health counseling unless you are a licensed therapist. Skip individualized nutrition plans unless you are an RD; coaching from USDA guidelines is fine.

The partner channel worth knowing about: Wellhub (formerly Gympass) runs a 55,000+ partner network and lets independent wellness pros list services. It won't replace direct sales but it can fill 1-2 sessions a week with corporate-paid attendees while you build your direct book.

Revenue Model

Solo wellness coach. You sell, you deliver, you bill. No staff in year one.

Month	Active contracts	Avg contract value	Monthly recognized revenue	Take-home (after platform fees, insurance, taxes ~30%)
Month 3 (first paid pilot)	1 kickstart + 1 retainer in negotiation	$2,000 (one-time)	~$2,000 (lumpy)	~$1,200-$1,400 (one-time)
Month 6 (book building)	2 retainers @ $2,000/mo + 1 kickstart pending	$2,000/mo each	~$4,500	~$2,800-$3,400
Month 12 (steady)	3 retainers @ $2,500/mo + 1 PEPM (60 employees @ $20)	mixed	~$8,700	~$5,800-$6,500

Two paths to the first $1K month. Sell one $1,500 kickstart challenge to a 40-person company — that is one good warm introduction and two meetings. The first $3K month means landing your first $2,500/month retainer plus a one-off lunch-and-learn ($500-$800). Most independents land contract one in months 3-5 because the B2B sales cycle from cold meeting to signed proposal averages 6-10 weeks even with warm intros.

A single 100-employee PEPM contract at $25/month is $30,000 a year of recurring revenue with one client to manage. That is the math that makes this business worth the slow start.

Startup Costs

Wellness coach certification — $399-$1,199. The NASM Certified Wellness Coach ($399-$599) is purpose-built for organizational delivery and the credential HR recognizes fastest. The ACE Health Coach ($699-$999) is the broader behavior-change credential.
WELCOA membership — $295-$595/year. The Wellness Council of America is the trade body HR people actually know. Membership gets you templates, the logo on your proposals, and access to the annual summit where mid-market buyers show up.
CPR/AED — $80-$120 every 2 years via American Red Cross or American Heart Association. Required only for in-person sessions, but procurement asks for it on the vendor checklist either way.
Insurance — GL + professional liability — $400-$1,200/year via Insureon or K&K Insurance. Corporate clients require $1M per occurrence and will ask to be named additional insured before you set foot on site.
Sales + delivery stack — $30-$100/month. Stripe for retainer billing (2.9% + $0.30/transaction), Typeform ($25-$50/month) for the employee baseline survey, Zoom Pro ($16/month), YuMuuv ($1-$3/employee/month) when running a paid challenge.
LLC + EIN + brand — $50-$500 LLC by state (LLC University 50-state table), $0 for EIN at IRS EIN Online, $400-$1,200 for a logo, Squarespace site, and a polished proposal slide template.
Background check — $25-$75 via Sterling Volunteers or Checkr. Required by most corporate procurement teams before site access.

Lean path: $3,000 (cert + insurance + Stripe + cheap site, no WELCOA in year one). Full setup: $9,000-$10,000 (cert + WELCOA + polished brand + first conference travel).

Legal & Formation

Business entity. Single-member LLC is the right answer. You are signing service contracts with companies that have legal departments and indemnification clauses — the personal-asset shield matters. File the LLC yourself through your secretary of state, then get your EIN free at IRS EIN Online. Apply free at IRS — never pay a third party. Put a CPA on retainer by month four; corporate invoicing means you'll owe quarterly estimated taxes from day one.

Licenses & sales tax. No state requires a specific license to deliver corporate wellness coaching. The credentials you carry (NASM CWC — Certified Wellness Coach, WELCOA, CPR/AED) signal legitimacy to procurement, not legal compliance. Services are generally not sales-taxable in most states. Physical wellness products you might resell (resistance bands, water bottles for a challenge giveaway) usually are. Confirm with your state revenue department before you bill the first retainer.

Industry-specific risk. The single biggest legal trap is incentive design under the ADA wellness rules and GINA. A $50 gift card for hitting a step goal is fine. A $1,500 health-insurance premium discount tied to a biometric outcome is not — it must be voluntary, the incentive cannot exceed 30% of the cost of employee-only coverage (50% for tobacco programs), and the data flow has to comply with GINA and ERISA. Your job is to spot the trigger and put a line in every proposal: "Programs tied to group health plan premiums require client's benefits counsel to confirm ADA, GINA, and ERISA compliance." Second trap: HSA/FSA does not pay for general fitness or wellness coaching. Under IRS Publication 502, only physical fitness prescribed by a physician for a diagnosed medical condition qualifies under Section 213(d). Don't promise HR teams that employees can pay you with HSA dollars. They can't.

Marketing & First Customers

Your first 5 contracts come from your LinkedIn, not from cold email. Make a list of 80 people in your network who work at companies with 50-500 employees, in HR, people ops, COO, or chief-of-staff roles. Message each one personally — not a templated pitch. "Hey, I just launched a corporate wellness practice focused on small and mid-market companies. Not selling — would love 20 minutes to ask what your team is actually doing right now and what's broken about it." Half won't reply. A quarter will take the call. One in ten of those calls turns into a paid kickstart.

Cold outbound works but slowly. Apollo or Hunter to find HR director emails at 100-300-employee companies in your metro, send 30 a week, expect a 2-4% reply rate and a 6-10 week cycle from first email to signed proposal. Skip mass blasts — every state with anti-spam enforcement under 15 USC §7704 (CAN-SPAM) has rules about commercial email, and HR people forward bad outreach to procurement as a blocklist.

The single highest-ROI move in year one is one well-rehearsed lunch-and-learn. Offer it free to two or three companies in your network. Walk in, deliver a sharp 30-minute talk on stress, sleep, or movement, leave a one-page proposal for a $2,000 four-week kickstart on the way out. Two of three will say "let me bring this to leadership." One will buy.

WELCOA membership earns its $295/year if you attend one summit and walk out with two warm introductions. Wellhub's partner application is worth filling out in month one — even one or two corporate-paid sessions a week through Wellhub is rent money while you build the direct book.

First 90 Days

Week 1: File LLC, get EIN, open business checking. Buy GL + professional liability ($400-$1,200/year) — name "Additional Insured" capability on the policy.
Week 1-3: Enroll in NASM CWC or ACE Health Coach. Pass within 6-8 weeks.
Week 2: Set up Stripe, Typeform, Zoom Pro, basic Squarespace site with three things only — your story, the three offerings, a contact form.
Week 3-4: Build your 80-person LinkedIn target list. Draft three message templates. Start sending — 5-10 personal messages a day, not a blast.
Week 4-6: Apply to Wellhub partner network. Join WELCOA. Build one polished 12-slide proposal template (problem, program, deliverables, pricing, timeline, references).
Week 6-10: Run two free lunch-and-learns at companies in your network. Each one gets a $2,000 kickstart proposal handed over before you walk out.
Week 8-12: Target: 1 paid kickstart contract signed by week 12. If you're at zero by week 14, the issue is the proposal — not the pipeline. Send your slide deck to three HR contacts and ask what would make them say yes.
Week 12: Set the 90-day book check. One signed contract = on track. Three meetings booked but no signature = your pricing or pitch needs a rewrite. Zero meetings = your LinkedIn outreach is too templated; rewrite from scratch.

Common Pitfalls

Selling to employees instead of HR. New wellness coaches build a beautiful consumer-facing pitch about transformation and feel-good outcomes, then can't close a single corporate contract. Fix: rewrite every piece of marketing to address one buyer — the HR director who needs ROI numbers and an engagement metric for the next board meeting. Lead with absenteeism, retention, and premium savings, not vague "wellbeing" language.
Promising HSA/FSA payment. Telling HR that employees can pay you with pre-tax HSA dollars sounds great in the pitch and gets you fired in month two when payroll bounces the claim. Under IRS Pub 502, general fitness coaching does not qualify under Section 213(d). Fix: remove every HSA/FSA reference from your materials unless you have a written physician-prescribed medical-necessity carveout, which is rare.
Walking into the GINA/ADA incentive trap. Your client says "let's offer employees a $1,000 premium discount for hitting a wellness goal." You say yes. Six months later the EEOC opens a complaint and the client points at you. Fix: any program tied to group health plan dollars goes back to the client's benefits attorney in writing — keep it in your standard proposal language and never, ever override it verbally.
Underpricing the first contract to "build a case study." A $500/month retainer for "logo rights" trains the buyer to expect $500 forever and signals to procurement that you are not a serious vendor. Fix: minimum first contract is $1,500 — a four-week kickstart at flat fee. If the buyer balks at $1,500 for a 40-person engagement, they are not your buyer; they want a free Slack challenge.

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