Why you are getting this
This is the full picture of where our marketing stands today, so your proposal can be scoped to what actually exists. It covers both of my brands, the assets you would inherit, the channels we use (and the ones we don't), and the rules any marketing has to follow.
Short version: we have real brand assets and a lot of finished client-facing work, but almost no consistent public marketing. Nearly all new business comes from referral partners and word of mouth. That is the gap.
The two brands
I run two sister companies. Pillar PEO Advisors pays the bills today; SMBHR is the growth bet and where most new marketing should go.
| Pillar PEO Advisors | SMBHR | |
|---|---|---|
| What it sells | Independent PEO brokerage: we shop and compare PEOs (outsourced payroll, benefits and HR) and help owners switch | HR for buying and running a business: HR due diligence before close, Day 1 transition, then fractional (part-time) HR on a monthly retainer |
| Who buys | Owners of 5 to 500 employee companies facing a health insurance renewal or unhappy with their current PEO | People buying a small business (often SBA-financed searchers), and owners of 10 to 150 employee companies with no full-time HR |
| How we get paid | The PEO pays us; no cost to the employer, disclosed in writing | Fixed fees agreed up front, never hourly |
| Started | 2025 | Formed as its own company October 2026 |
| Website | pillarpeo.com, live | smbhr.com, live but hidden from Google until launch |
| Brand | Navy and bright green, League Spartan | Deep green and chartreuse, Plus Jakarta Sans, finalized Nov 4, 2026 |
The two refer to each other. SMBHR's site sends PEO and benefits questions to "our sister company, Pillar PEO Advisors." Pillar's PEO clients are natural fractional HR clients. Before SMBHR existed, the HR work was sold as "Pillar HR," so you will see that name in older material.
Where we are today
We are small, busy and almost entirely referral-fed. Marketing gets funded before any new hire: we agreed in October not to hire until SMBHR has six monthly retainer clients.
Volume right now
- About 35 PEO quotes in progress on the Pillar side.
- Four monthly fractional HR clients on the SMBHR side, plus project work on acquisitions that are closing now.
- SMBHR's free offer for buyers, "Day One Ready," is being set up as a standing program with an M&A law firm.
Team
| Person | Role | What it means for marketing |
|---|---|---|
| Caleb Sherrill | Founder of both companies; sales, partnerships, pricing | The public face. Wants to move toward speaking and national partnerships and out of client delivery by 2029. Time is the scarcest thing we have. |
| Lui Prieto | Co-founder and Chief People Strategist, SMBHR | Delivers most of the HR work. Over a decade in HR and people roles, fully bilingual English and Spanish. A second voice for content. |
| Emily | Part-time operations, Pillar PEO side | Runs PEO intake and quote tracking. Not part of SMBHR. |
Josiah Sherrill, an early co-founder of Pillar, left in October 2026. He is still named on pillarpeo.com.
How clients find us today
- Benefits brokers who send us their groups to shop PEOs. One firm alone has sent about 20 groups since late September.
- Deal people: M&A attorneys, quality of earnings (QoE) accountants, finance and CPA firms, SBA lenders.
- The Charlotte ETA Group, a 500+ member community of people buying and running small businesses. I am its Executive Director.
- Conferences. One trip to SMBash in Dallas produced five opportunities and our best referral relationship.
- Podcast guest spots and speaking.
None of this is tracked well. Our CRM has a referral source on 8 of 123 opportunities, so we know who sends business from memory and email, not data.
Who we sell to
We decided on Oct 28 to lead SMBHR's marketing with acquisition deals and let fractional HR follow, because a buyer who uses us for the deal usually stays on as a monthly client.
Buyers and owners
| Audience | Their moment | What they worry about |
|---|---|---|
| Searchers and first-time acquirers (SMBHR) | Under LOI on a 10 to 150 employee business, usually SBA-financed | Key people leaving, back overtime, unwritten promises to staff, benefits and insurance that reset at close |
| Owners of 10 to 150 employee businesses (SMBHR) | Growing past what the owner can handle on HR | Compliance mistakes, handbooks, hiring and firing, no one to call |
| Owners of 5 to 500 employee companies (Pillar) | Health renewal just went up, or their PEO is letting them down | Cost, switching effort, "are we too small," how the broker gets paid |
Referral partners are an audience too. Much of our marketing has to make it easy for these people to introduce us: M&A attorneys, QoE accountants, SBA lenders, finance and CPA firms, and benefits brokers. A new SBA rule (effective Oct 1, 2026) requires a QoE report on SBA loans of $3M and up, which puts more deals in front of QoE firms that do not cover HR.
What owners actually ask me. I counted the questions across 35 recorded first calls about PEOs:
| Question | Times asked (approx.) |
|---|---|
| Is it more expensive? | 23 |
| How is Pillar paid? | 20 |
| How hard is switching, and when? | 19 |
| How is this different from my payroll company, and which PEO? | 17 |
| Are we too small? | 16 |
| What data do you need? | 15 |
Those questions are ready-made content.
What sets us apart: we find money in the deal, we have PEO and benefits expertise in-house, we work closely with deal teams, we serve clients in English and Spanish, and our prices are fixed. The only HR firm we know of that targets acquisition buyers is Amplēo. Most PEO and payroll brands are blue or red, which is part of why SMBHR went green.
Brand and creative assets
SMBHR has a finished, current brand kit. Pillar has an older 2025 kit that still works but has not been refreshed. Neither brand has video, a photo library or a content archive yet.
SMBHR (current, finalized Nov 4, 2026)
| Asset | What exists |
|---|---|
| Logo | "SMBHR" wordmark with crop-corner brackets around HR. Versions for light, dark, one-color charcoal, one-color deep green and neutral, in SVG and PNG |
| Icon | HR icon in square, circle and on-chartreuse versions; favicon and app icon |
| Colors | Deep Green #082824, Soft Chartreuse #CBDE4F (highlight #B9CC3E), Warm Neutral #F7F4EC, Charcoal #2C2C2C, Sage #A7B8A3, Deep Olive #5E6B10 for small text on light backgrounds |
| Type | Plus Jakarta Sans |
| Social kit | LinkedIn company logo and banner, personal LinkedIn banner, Google Business logo and cover, profile pictures, website share image, email signature logo |
| Guidelines | A brand guidelines page with logo rules, color, type and the social files. I can share it with you |
| Messaging | Tagline in use: "The people side of the deal." Descriptor: "HR for buying and running a business." Alternatives such as "HR for the deal and the day after" are still on the table |
The brand went through several rounds in October (gold, then amber and cobalt) before landing on deep green and chartreuse. That palette came from an outside brand kit by Dakota Milner at Rev Innovate. Treat it as settled.
Pillar PEO Advisors (2025)
- Logo: lowercase "pillar" wordmark in League Spartan with a green circular icon, versions for light and dark backgrounds.
- Colors: navy #000850 and green #30D070. Body font in the guidelines is Garet.
- Brand guidelines PDF made in Canva, February 2025.
- A design system folder with a pitch deck, a PEO 101 explainer deck, and one-pagers ("Already on a PEO," "PEO Responsibilities," "Referral Partner").
- Three stock photos and some LinkedIn banners and speaker-promo slides from 2025.
Photos
- Professional headshot of me, plus photos of Lui and Emily.
- Eight client logos already on the SMBHR site.
- No other photography. I have rejected stock photos on both sites.
Websites, pages and content already built
We have built far more than we have marketed. Most of it was made for one client or one partner meeting and has never been repurposed into public content.
| Asset | What it is | Status |
|---|---|---|
| smbhr.com | Full site: buyer pages (Day One Ready, HR due diligence, transition support, first 100 days), owner pages (fractional HR, HR Health Check, projects, payroll systems), partners, pricing, state and industry pages, a due diligence checklist | Live, hidden from Google. Target for full launch is end of November. Pricing still being finalized |
| pillarpeo.com | PEO brokerage site: how it works, switching PEOs, PEOs for nonprofits, first-time PEO, FAQ, resources | Live. Built on Lovable. Has Google Analytics and a chat widget. Messaging is dated and still lists Josiah |
| HR Headache Score | Short quiz on pillarpeo.com (pillarpeo.com/hr-headache-score) | Live |
| HR Health Assessment | Longer self-assessment that captures leads and gives me a private brief on each company (pillar-hr-assessment.pages.dev) | Live, Pillar branded |
| What Is a PEO? | Interactive walkthrough I present to owners: how a PEO works, the cost, fit check, switch timeline, 17 FAQs (pillar-what-is-a-peo-wqaiik.pages.dev) | Live, link only |
| Day One Ready | SMBHR's free offer for buyers: 10-question intake, 20-minute call with Lui, one-page memo, with a made-up sample memo | Pitch page and buyer page built |
| Partner pages | One custom page per referral partner type: M&A law firm, QoE accounting firm, finance and CPA firm, benefits broker guide | Built, private links |
| Client review pages | A house format for PEO renewal comparisons. Dozens built since September | Confidential, never public |
| Sales collateral (PDF) | Pillar pitch deck, sales playbook, broker partner presentation, monthly partner report, sample savings report, client submission checklist | Exists, 2025 era |
| Speaking | A Charlotte ETA keynote deck, "Don't Lose Your Best People" | Exists |
The client pages show what our work looks like better than anything else we have. They cannot be shared, but the format and the anonymized patterns behind them can become content.
Channels today
The honest answer is that no channel runs on a schedule. The plan Lui and I set in October was LinkedIn at 3 to 5 posts a week, two ETA conferences as a test, and a launch to my existing PEO network. None of it is running on a schedule yet.
| Channel | Status today | Notes |
|---|---|---|
| LinkedIn, my personal profile | No regular posting cadence | The most valuable channel we have. Deal people and owners look me up before they reply |
| LinkedIn, Lui's profile | Set up, no regular posting | Lists her as co-founder |
| LinkedIn company pages | SMBHR page not created yet | An inactive HR firm in Monroe, NC with the same name holds the "SMBHR" page. We are sorting that out before claiming or creating one. Logo and banner are ready |
| X / Twitter | No account for either brand that I know of | You raised it. I would want to hear why it fits this audience |
| About 400 contacts in an old MailerLite list from 2025 | No newsletter. Referral partners are not on a list | |
| Paid ads | None running | Never tested in a structured way |
| Events and speaking | Executive Director of the Charlotte ETA Group, monthly events. SMBash Dallas worked well. Podcast guest in March 2026 | Charlotte ETA has its own brand and designer, and we keep Pillar and SMBHR sales messages out of it on purpose |
| Google Business Profile assets made, not set up. smbhr.com not yet submitted to search | Planned for launch | |
| Partner co-marketing | Custom partner pages and a broker guide | The M&A law firm program will put SMBHR in every buyer's welcome email once it is live |
Tools you would work alongside
I build most of our pages, sites and documents myself with Claude (an AI assistant), so a good partner can hand me copy and direction and I can ship quickly.
| Tool | What we use it for |
|---|---|
| Claude and Claude Code | Building sites, client pages, decks and documents |
| Cloudflare | Hosts smbhr.com and all our client and partner pages |
| Lovable | Hosts pillarpeo.com |
| GoHighLevel | CRM with pipelines and a website chat widget. Not used consistently since September. No social accounts connected |
| Fathom and Wispr Flow | Record and transcribe my calls. Hundreds of hours of real owner and buyer conversations, a deep source of content ideas |
| Google Workspace | Email for pillarpeo.com and smbhr.com, Drive, Calendar |
| monday.com | Client project boards |
| Canva | Older Pillar graphics |
| ZoomInfo | Company and contact research |
| Google Analytics | Installed on pillarpeo.com |
Rules any marketing has to follow
These are firm. Most come from confidentiality, legal limits, or lessons from things I have already rejected.
Confidentiality
- No client names, deal details or numbers in public content, even anonymized. Posts use hypotheticals ("Picture a 30-person shop...") or patterns ("I see this all the time"). Never present a hypothetical as a real recent client.
- Some partners white-label our work under their own name. Those deals are never mentioned anywhere.
- Case studies or testimonials only with written permission from the client.
Legal and industry limits
- Pillar always discloses how it gets paid. SMBHR is never described as a broker.
- Attorneys in North Carolina cannot pay or swap referrals. Co-marketing with law firms is "recommend each other on merit," no referral fees or exclusivity.
- Charlotte ETA messaging stays free of Pillar and SMBHR sales pitches. Panelists' employers are not named publicly without their OK.
- Lui's experience is described as "over a decade." Not 15 or 17 years.
Voice
- Plain, short and human. It has to sound like me, not like AI. Stock phrases, hype and clipped two-part slogans get cut.
- No em dashes, anywhere.
- The name is written "SMBHR," one word.
Visual taste (what I have rejected so far)
- Generic icon sets, emoji-style icons, sparkles and handshakes. They read as AI-made.
- Stock photos of people. Real photos of Lui and me work better.
- Swoops and people pictograms in logos. I like boxy and clean.
- Bar and waterfall charts for money. Plain number tables read faster for owners.
- Walls of text. Each section should fit one laptop screen.
Approvals: I approve anything published under my name or either brand until we have built trust.
Gaps and open decisions
The biggest gap is consistency: we have the material and the expertise, but no one owns turning it into a steady public presence.
- No content engine. My calls are full of usable lessons, but nothing turns them into posts. My time is the bottleneck, so the system has to work with minimal input from me.
- SMBHR launch. The site goes public around the end of November. It needs launch content, a LinkedIn page and Google setup.
- SMBHR name on LinkedIn. The same-name company page has to be resolved, or we pick a distinct page name.
- Pillar refresh. pillarpeo.com messaging is dated, still lists a co-founder who left, and does not match SMBHR's quality. Open question: how much to invest in Pillar versus SMBHR.
- Pricing. SMBHR's public prices are being finalized by Nov 30. Messaging can start before that.
- Proof. We have eight client logos and no written testimonials or permissioned case studies yet.
- Tracking. We do not know which channel produces what. The CRM is not used consistently.
- Partner kit. Referral partners need something easy to forward: a one-pager, an intro email, a short explainer.
- Paid ads. Untested. Our audience is narrow (acquisition buyers, deal advisors, owners of 10 to 150 person businesses), so I want a view on whether ads are worth it now, and where.
- Taglines and messaging. "The people side of the deal" is working for buyers. We do not have an equally sharp line for owners.
What I would like to see in your proposal
I want a clear first 90 days and a monthly price, with options I can choose between.
- Your read on priorities. Which brand, audience and channel you would start with, and why. Push back where you disagree with our October plan.
- First 30 days. What you would set up: positioning and messaging, LinkedIn pages and profiles for Lui and me, the SMBHR launch, a partner kit.
- Ongoing work. What a month looks like: posts per week by channel, who writes them, how you would pull ideas from my recorded calls, design work included.
- Paid ads. Whether you recommend them now, which platform, a test budget, and what success looks like.
- Time from me. How many hours a week you need from me and Lui, and how approvals work.
- Measurement. What you would report monthly, and what you need from our CRM and sites.
- Pricing options. Two or three levels with what each includes, the minimum term, and who owns accounts, files and content if we part ways.
- Start date and anything you need from us before you begin.
Open question: I will share a monthly budget range directly.