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AI-Powered Executive Support

Most AI assistants just generate text. ChiefDesk actually does the work.

ChiefDesk turns your notes into strong working drafts — proposals, operating systems, and strategic plans — for your team to review and finalize.

Funders want confidence that your organization can execute. AIChiefDesk helps strengthen the back office, improve operational readiness, and build the systems that support sustainable growth.

Starter, Growth, and Nonprofit Pro include a 14-day free trial.

Book a Demo

Tell us about your organization, and we’ll be in touch to schedule a time.

What ChiefDesk Does

Your AI-powered workspace for executive operations and business development workflows

Built for leaders who are great at their mission but need structured workflows to document, fund, and scale it. ChiefDesk turns your priorities into polished, actionable documents — without adding headcount.

Operations documentation & SOPs
Grant proposals & funder narratives
Strategic plans & OKRs
Board updates & presentations
Email composition & stakeholder updates
HR templates & employee handbooks
Business proposals & pitch decks
Workflow automation design
Research briefs & competitive analysis
Meeting prep & executive summaries

Who It's For

Leaders who need world-class operating workflows

ChiefDesk is built for executives and founders who are brilliant at their craft but need structured help with the documents, systems, and communications that keep a business running.

Entrepreneurs & CEOs
Use ChiefDesk to organize investor updates and operational systems in one workspace.
Nonprofit Leaders
Keep mission work at the center. Draft grant proposals, board reports, and donor communications with structured support.
Consultants
Deliver more value to clients. Generate project plans, status reports, and professional deliverables with repeatable workflows.
Social-Impact Founders
Build the infrastructure your mission deserves. Turn ideas into fundable proposals, scalable systems, and real documents.

Designed for the operator’s week.

ChiefDesk is designed for the work of nonprofit and community leaders who need board updates, funder narratives, and operating documents to move on time.

For hands-on consulting, visit YW Consultants →

Built from operating experience

  • Structured support for nonprofit leaders
  • Grew Timelist Group's budget from $4M to over $9.5M (2022–2025).
  • Advises government, nonprofit & community orgs

Product workflows

What ChiefDesk produces

Software capability

AI grant and proposal workflows turn a guided brief into a source-grounded working draft for review.

ChiefDesk software feature

Software capability

ChiefDesk keeps operating documents, board updates, and funder narratives in one repeatable workspace.

ChiefDesk software feature

Software capability

Workflow templates help teams create polished documents without adding headcount.

ChiefDesk software feature

Pricing

Invest in your operations — from $49/month. Nonprofit Pro for eligible 501(c)(3)s: $299/month.

No seat limits, no per-document fees. Pick the tier that matches where you are and scale as you grow. Every tier is ChiefDesk software, with product support matched to the plan.

Source-grounded grant drafts for review
Weekly board update auto-generated
Operational SOP from a 15-minute brief
Nonprofit Pro – Mission Pricing
Nonprofit Pro
$299/month
Registered 501(c)(3) organizations with annual budgets under $5M.
  • Everything in Growth
  • Unlimited grant proposals (all 3 formats)
  • AI grant & proposal generator
  • Unlimited PDF exports
  • Strategic plans & OKR templates
  • Board reports & donor communications

Or if you want to confirm eligibility before subscribing

Add-on availableAdd the Team Training tracks →Guided training tracks to onboard your team on ChiefDesk workflows — contact us for pricing.

Starter
$49/month
Solopreneurs and early-stage founders getting off the ground.
  • Unlimited document drafts
  • Email composition support
  • Strategic planning templates
  • Basic workflow templates
  • 10 exports per month
Most Popular
Growth
$199/month
Small businesses and nonprofit leaders with active operations.
  • Everything in Starter
  • Advanced document creation
  • Grant & proposal support
  • SOP & HR admin templates
  • Strategy support
  • Unlimited exports
Executive
$750/month
CEOs, agencies, and high-volume teams ready for priority AI response time, customized workflows, guided setup of your ChiefDesk workflows, priority product support, and quarterly product and workflow reviews.
  • Everything in Growth
  • Priority AI response time
  • Customized workflows
  • Guided setup of your ChiefDesk workflows
  • Priority product support
  • Quarterly product and workflow reviews

Add-on availableAdd the Team Training tracks →Guided training tracks to onboard your team on ChiefDesk workflows — contact us for pricing.

Nonprofit Pro – Mission Pricing

Apply for nonprofit pricing

For registered 501(c)(3) organizations (or equivalent) with annual budgets under $5M. Fill out the short form below — we review applications within 2 business days and send your subscription link directly.

✓ US 501(c)(3), Canadian CRA-registered, UK Charity Commission, or equivalent

✓ Annual operating budget ≤ $5M

✓ Account used for the nonprofit's own operations (not a consulting agency)

How It Works

From task to deliverable in three steps

01

Answer guided questions

Describe what you are working on — a grant proposal, a hiring policy, a quarterly report. The more context you give, the better the output.

02

AI generates your documents

ChiefDesk produces complete, tailored drafts — not generic templates. Every document matches your context, your audience, and your voice.

03

Review, refine, implement

Edit, regenerate, or approve until it is right. Then export as a PDF, send directly, or plug it into your existing workflow.

The ChiefDesk Approach

Software that fits the way you work

Not every leader needs the same level of support. Our tiers are designed to scale with you — from independent document generation in Starter/Growth, to guided setup of your ChiefDesk workflows in Executive. Multi-team ChiefDesk deployment, custom workflows and admin controls. Contact us for pricing.

vs. LindyNo surprise billing. ChiefDesk pricing is flat and predictable — no per-action charges that balloon as you scale.
vs. XemblyWe're not going anywhere. ChiefDesk is built for long-term operations, not an acquihire waiting to shut down.
vs. generic AI assistantsWe don't stop at text. ChiefDesk produces complete, ready-to-use deliverables — proposals, SOPs, plans — not just suggestions.

Not sure which tier is right for you?

Book a 30-minute demo and see ChiefDesk on your real workflows.

Book a Demo

ChiefDesk updates

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FREQUENTLY ASKED

Questions worth answering before you sign up.

The seven objections we hear most from executive directors, founders, and chiefs of staff.

ChiefDesk produces complete, tailored documents — proposals, briefs, follow-ups — grounded in your organization’s context, not a blank chat window. Think of it as a chief of staff that already knows the board, the donors, and the deadlines.

Want the detailed version?

Read the full FAQ.

Direct answers to the questions nonprofit leaders raise most often — setup, data, cancellation, and how ChiefDesk compares to hiring an EA.

Open the FAQ →

ChiefDesk updates

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