For business & leadership coaches

Software for business and leadership coaches

Engagement letters, multi-month retainers, contracts, time tracking, and a branded client portal. Built for coaches running B2B engagements and corporate development programs.

ENGAGEMENT LETTER 6-Month Executive Coaching Engagement
C
crestline
Prepared by
Crestline Coaching
Executive & Leadership Practice
Presented to
Brightline Capital
Sarah Chen, Chief People Officer
Engagement start
Jun 1, 2026
Through
Nov 30, 2026
Scope
6-month executive development engagement for VP Finance: 360° assessment, biweekly 1:1 coaching, stakeholder review, and quarterly progress reporting to CPO sponsor.
ComponentTermMonthlyAmount
Discovery, 360° & program designOne-timen/a$9,500
Monthly executive coaching retainer6 months$7,500$45,000
Engagement total USD $54,500
Sarah Chen · CPO, Brightline Capital
Countersigned
May 24, 2026
Invoice #064 Sent
Brightline Capital
Aug coaching retainer $7,200
360° assessment debrief $1,800
Due in 14 days $9,000
Retainer Active
Hadley Group: Leadership Cohort
Monthly $12,500 / month
Next invoice Renews in 12 days
Time · This week Live
28 hrs logged
Across 6 engagements · 3 corporate
Top client Brightline Capital

You're a coach, not a billing administrator.

Calendly handles the booking. Zoom handles the sessions. But the engagement letter lives in a Google Doc you copy-paste from your last engagement. The contract goes through DocuSign. Monthly invoices come out of QuickBooks (or a spreadsheet, if you're being honest). Retainer balances live in a Notion table you update Sunday nights. The HR sponsor at your corporate client doesn't have a clean way to see status, so they ping you.

Clientary replaces the operational layer of a coaching practice: engagement letters, contracts and NDAs, multi-month retainer billing, time tracking, branded client portals, and online payments in one place. Keep your scheduling tool. Keep your video tool. Let Clientary handle the client-facing operations.

Built for the way coaching practices actually work

Whether you're a solo executive coach or a 12-person coaching firm running corporate programs, the workflow fits engagement-based, retainer-billed practices.

Executive Coaching

C-suite and senior leadership engagements, transition coaching, 360°-driven development. Multi-month retainers with quarterly stakeholder reporting.

Leadership Development

Emerging leaders, manager-to-leader programs, high-potential cohorts. Program-based engagements with cohort participants and per-cohort billing.

Business & Founder Coaching

Founder coaching, growth and scaling guidance, board-prep work. Monthly retainers with engagement-letter framing for board legitimacy.

Team & Group Coaching

Cohort programs, team offsites, group coaching pods. Multi-participant engagements billed to a single corporate sponsor with clean reporting.

Corporate Training & L&D

Leadership training, soft-skills curricula, train-the-trainer programs. Workshop-based fees, multi-cohort rollouts, and quarterly enterprise invoicing.

Coach Mentoring & Supervision

ICF mentor coaching, supervision practices, and coach training programs. Cohort-based engagements with recurring monthly billing.

The practice operations stack you've been duct-taping together

Engagement letters that read as professionally as your work

Send a polished proposal with engagement scope, phase breakdown, and optional add-ons. The client signs the contract or NDA online. Approved engagements convert to a project in one click. The engagement you proposed becomes the engagement you track.

Monthly coaching retainers on autopilot

Multi-month engagements are a natural retainer model. Set the monthly amount, automatic recurring invoicing handles billing, and the client sees their balance and engagement status in the portal. No more "did we get August's invoice out?" Sunday-night ritual.

Branded client portal for HR sponsors and coachees

Every client (or corporate sponsor) gets a branded portal under your practice's identity. They view the engagement letter, sign contracts, see invoice and payment history, and track engagement progress. It signals the kind of operational discipline enterprise clients expect from a premium practice.

Contracts, NDAs, and confidentiality agreements built in

Executive coaching engagements live or die on confidentiality. Built-in contracts and e-signatures handle coaching agreements, NDAs, and statements of work. Documents sign and store online. No separate DocuSign subscription, no document version control through email.

Track session and prep hours without the spreadsheet

One-click timers log sessions, prep, and reflection time per engagement through time tracking. Useful for understanding real engagement load, for tracking utilization across a multi-coach firm, and for the rare engagement that bills by the hour.

Project management for cohort programs and multi-month engagements

Cohort programs, multi-participant engagements, and long-running development work all need structure. Projects with milestones give you (and the corporate sponsor) clear visibility into where each engagement stands.

10,000+
Service businesses run on Clientary
$500M+
Invoiced through the platform
4.8/5
Average rating across review sites

“TERMA is a global team of ICF-certified executive coaches working quietly with the world's top public companies. What we appreciate most about Clientary is the simplicity of the interface and that it ALWAYS WORKS. Very reasonable subscription fee, all the functionality we need, and none that we don't.”

TERMA · global executive coaching practice serving Fortune 500 clients · Read the full story →

Frequently asked questions

Common questions from executive coaches, leadership coaches, business coaches, and coaching firms evaluating Clientary.

What software do business and leadership coaches use to run their practices?

Most coaching practices stitch together Calendly for booking, a Google Doc for engagement letters, DocuSign for the contract, Stripe for one-off payments, QuickBooks for the books, and a spreadsheet for engagement tracking. Clientary replaces the operations layer: engagement letters, multi-month retainer billing, contracts and NDAs, time tracking, a branded client portal, and online payments. The only thing coaches keep separate is their session scheduling tool.

Is Clientary a session-scheduling or video-call tool?

No. Clientary is the business operations and client-facing layer. Pair it with Calendly, Acuity, or your existing scheduling tool for session booking, and Zoom or Google Meet for the sessions themselves. Clientary handles everything around the sessions: engagement contracts, retainer billing, time logs, invoicing, and the client portal.

Can I bill monthly coaching retainers automatically?

Yes. Multi-month coaching engagements are a natural retainer model. Set up a monthly retainer per client (or per cohort program) with automatic recurring invoicing. Clientary tracks the balance, gives the client visibility through the portal, and sends the next invoice on schedule without intervention.

Does the client portal work for ongoing coaching engagements?

Yes. Every client (or corporate sponsor) gets a branded portal under your practice's identity where they view the engagement letter, sign contracts, see invoices and payment history, and track retainer balance month-over-month. For B2B engagements with HR or L&D sponsors, it reads as the kind of operational discipline enterprise clients expect.

Can I handle confidentiality agreements and NDAs for executive coaching?

Yes. Built-in contracts with e-signatures handle confidentiality agreements, coaching agreements, statement-of-work documents, and any NDAs the client legal team requires. Documents sign and store online, no third-party DocuSign account required.

Does Clientary work for both solo coaches and coaching firms?

Both. Solo executive coaches use it as their full back office. Multi-coach firms add team members with role-based permissions so each coach manages their own clients and engagements while practice owners get firm-wide reporting on revenue, retainers, and engagement load.

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