Two rooms · choose yours

A peer forum for Massachusetts small business CEOs

The room where CEOs stop guessing.

Running a small company is the loneliest job in the building. The Small Business Roundtable puts you in a confidential, NDA-bound room with peers carrying the same weight — twelve months of monthly sessions built on one shared priority: top-line growth.

Request a seat

→

How the grant covers it

Membership is by application. Seats are limited to keep the room honest.

100%

Reimbursable through the MA Express Grant

20+

Growth frameworks and a
Growth Workbook

Format

Monthly · in-person & virtual

Built for

One-year membership

Commitment

One-year membership

Confidentiality

NDA-bound

Investment

Grant-eligible in MA

A peer forum for Massachusetts nonprofit Executive Directors

The room where Executive Directors stop carrying it alone.

You answer to a board, a staff, a donor base and a community — and there is rarely anyone to think out loud with. The Nonprofit Roundtable puts you in a confidential, NDA-bound room with fellow Executive Directors for twelve months of monthly sessions built on growing your reach and your revenue.

Request a seat

→

How the grant covers it

Membership is by application. Seats are limited to keep the room honest.

$12K

Annual membership — funding routes we map with you

20+

Growth frameworks and a
Growth Workbook

Format

Monthly · in-person & virtual

Built for

Nonprofit Executive Directors

Commitment

One-year membership

Confidentiality

NDA-bound

Investment

Funding routes we map

Who this is for

Collaborate to innovate
and grow.

This is not a networking breakfast and it is not a mastermind selling you a framework.It is a working group of small business CEOs who put real numbers and real problemson the table, under agreement, and leave with decisions.

Tap into peer wisdom

Explore industry trends

Build lasting connections

03 — The Results

Helping CEOs tackle themost pressing growthchallenges.

Every session is built and facilitated around one question: what will move your top line in the next ninety days? Nothing on the agenda that doesnot serve that.

01 — Top line

Revenue-focused by design

Every session is dedicated to strategies that move the top line. Not culture workshops, not vision exercises — growth, with numbers attached.

02 — Your peers

Built only for small business CEOs

Tailored exclusively to leaders facing the same growth obstacles, which is why the advice in the room is relevant instead of borrowed from the enterprise playbook.

03 — In the room

In-person engagement

Immediate, interactive feedback and discussion. You leave with solutions shaped around your situation, not a recording to watch later.

04 — You keep it

Frameworks and tools you keep

Exclusive access to 20+ tested growth strategies, sales playbooks and marketing best practices — plus the Growth Workbook, built for small business.

03 — The Results

Five things that make the room work.

Structure is what separates a peer forum from a coffee meeting. These five rules are non-negotiable, and they are why members speak candidly from the first session rather than the sixth.

Peer collaboration

Exchange growth strategies with fellow members in a confidential setting built on trust and shared experience.

Targeted growth strategies

Every session is focused on strategies that drive revenue growth and solve the toughest problem currently on your desk.

Comprehensive resources

Access to over 20 business frameworks and an exclusive Growth Workbook designed to make the work repeatable after the session ends.

Confidentiality

All members sign NDAs. Open, honest and secure discussion is the whole product — without it the room is worthless.

A yearly commitment

One-year membership. Deep collaboration and compounding growth need a runway that shorter formats cannot give.

04 — Outcomes

Expand and thrive.

What membership is meant to produce inside the first year. These are the goals the sessions are organized around — not guarantees, but the scoreboard we hold the year against.

Outcome 01

Revenue growth

Substantial top-line growth within the first year through targeted, peer-tested strategy.

Outcome 02

Market expansion

The expertise and tools to reach new regions and adjacent audiences with confidence.

Outcome 03

Increased market share

A larger customer base and a fortified competitive position in an industry that keeps getting louder.

Outcome 04

Sharper pipeline

Faster conversion through a refined, high-performance outreach strategy that lifts efficiency.

05 — The Funding

$12K a year, reimbursed by the state.

Massachusetts small businesses can recover the full cost ofmembership through the Workforce Training Fund ExpressGrant. Our Grant Administrator walks you through the wholeprocess — the application itself takes about fifteen minutes.

Annual membership

$12,000

Covers monthly sessions, expert coaching, one-on-one time, 20+ growth frameworks and the Growth Workbook.

Grant administered by Commonwealth Corporation. Award subject toeligibility and approval. Skayle 360 does not control grant outcomes.

15 minutes

Apply

Our Grant Administrator guides your organization through the entire grant process in well under an hour — we help fill out the paperwork and submit the application.

~3 weeks

Wait for approval

After submission, all that is left is the approval letter from the Express Grant Training Fund. That typically takes about three weeks.

~5 weeks

Submit for reimbursement

After your first three Roundtable sessions, submit proof of payment with our Grant Administrator’s help. Reimbursement lands in roughly five weeks.

Start the grant conversation

Run the 30-second eligibility check →

06 — Questions

Before you apply.

If your question is not here, ask it on a call. A seat only worksif the fit is right in both directions.

Talk to Chris

→

What makes the Skayle 360 Small Business Roundtable different?

It is built exclusively for small business CEOs, so the discussion stays on the obstacles that come with running a company of your size — and every session is pointed at top-line revenue growth rather than general leadership development.

How is confidentiality maintained?

Every member signs a confidentiality agreement. That is what makes it possible to put real numbers, real personnel problems and real strategic doubts on the table from the first session instead of the sixth.

What topics get discussed?

Growth strategies: market expansion, sales optimization, AI integration and leadership development. Members shape the agenda around what they are facing, and Chris brings the framework that fits it.

What is the commitment level?

A one-year membership. Shorter formats do not build the trust that makes peer advice worth taking, and they do not give a strategy long enough to show results.

How often do you meet?

Monthly, in person and virtually. Each session is structured to send you out with an actionable decision rather than a page of notes.

What does it cost?

The annual membership fee is $12,000, covering monthly sessions, expert coaching, one-on-one time and exclusive access to the growth resources. Massachusetts organizations can typically recover the full amount through the Express Grant.

Is one-on-one coaching included?

Yes. Beyond the group sessions, members get personalized one-on-one coaching to work through challenges specific to their organization and refine strategy between meetings.

How does this actually help my business grow?

You get 20+ tested growth frameworks and the Growth Workbook, plus the collective experience of CEOs who have already solved the problem in front of you. Most of the value comes from the second — someone in the room has usually done it.

07 — Get Started

Talk to someone who has done it.

If reading other people's reviews only goes so far, ask for areference. We will put you in touch with a past participant in yourindustry or roughly your size — no script, no minder on the call.

See the program

→

Phone

(888) 209-1360

cciunci@skayle360.com

Office

399 Boylston Street, Boston, MA

/in/christopherciunci/

Thank you! Your submission has been received!

Oops! Something went wrong while submitting the form.

Leading a nonprofit instead?

There is a separate room for Executive Directors.

The Nonprofit Roundtable runs the same format with the same facilitator, but the table is all Executive Directors — so the conversation is donor base, board dynamics and community awareness rather than sales quotas.

View the Nonprofit Roundtable

Not ready for a roundtable seat?

Most organizations start with SCALE UP.

Fifty hours across strategy, team, marketing, lead generation and AI — fully funded by the Express Grant for qualifying Massachusetts employers. Build the operating system first, then bring it into the room.

Explore SCALE UP

See the five modules