Earlier at dinner someone asked me how I design my fractional CMO engagements and structure, and it’s been asked enough at this point that I decided to document it (with the help of a portfolio analysis and AI). The general answer is that it evolved across clients. I wrote the prototype as a proposal in August 2021, five years before I’d call myself a fractional CMO, and at the time it wasn’t a model at all. It was just the proposal I needed to write to get rehired by a former client for the conference I’d been running.
In this case study I’ll go over how the freelance-return engagement that grew out of my Deliverr exit became the template every fractional engagement I’ve designed since.
What I built at Deliverr, 2018-2021
To understand why the August 2021 proposal worked, it helps to know what I’d already done at Deliverr by the time I wrote it. Every line in that proposal was something I’d already shipped, measured, and watched succeed across three years of FTE work.
2018: Building a foundation from zero
I joined Deliverr two months before the public launch (April 17, 2018), when the company was 15 people. My first deliverable was a four-part pre-launch strategy I’d sent Michael Krakaris (Co-Founder) the day after our first meeting, covering pre-event social setup, optimized site copy with comprehension keywords, see-think-do blog content, editorial calendar, and success metrics. None of that was in the job description; I wrote it as the recap that won me the engagement.
By the end of 2018:
- Blog launched. Domain Authority grew from 7 to 27 in 8 months.
- Newsletter went from 86 subscribers in May to 1,154 by December; 13x growth in seven months.
- Went from one published guest post in May to 28 by December.
- Michael’s Q4 2018 review: “Be Lean: 10/10. The amount of content Deliverr pushes out on weekly basis exceeds that of any other players in the space. And we do this with one of the smallest teams.”
The lean-execution pattern that later anchored the 2021 proposal’s budget discipline was already the managerial signature by the end of year one.
2019: Audience signals: Shipping customer-led growth
The Walmart Marketplace email course was the year’s defining build. I’d noticed that webinar Q&As, newsletter replies, and inbound seller questions were all clustering around one topic; selling on Walmart Marketplace. Three independent signal sources saying the same thing. Without a brief, budget approval, or manager direction, I built a 6-part email course assembled from existing Deliverr blog posts, videos, and Walmart partnership content. 400+ signups in the first month. That course became the proof-of-concept for the email-course lineup behind it (Multi-channel 101, Shopify, Wish) that got us 1,500+ unique subscribers across the lineup by 2020.
Michael’s 2019 review on the launch: “Rachel set up multiple email courses for sellers, which included really helpful information on marketplace selling and has had solid adoption today. It was also an idea she thought of on her own, which demonstrates strong creativity.”
The autonomous-decision pattern (see signal, ship response, measure outcome) became one of my favorite ways to work, and led me to the Customer-Led Growth course I took later.
2020: The flywheel + flagship event
By 2020, my title was Senior Acquisition Marketing Manager covering content marketing (blog, newsletter, longform, SEO), email marketing, event coordination (webinars + Discoverr), affiliate program, website optimization, and partner marketing. Through Series A, B, and C, I ran all of these functions alone, supported by a managed contractor stack of writers, designers, partner contacts, and developers.
The numbers from this year:
- Blog pageviews: 6× YoY growth (per my 2020 manager review)
- 50+ videos produced
- 80+ webinars across tenure
- Newsletter to 45,221 subscribers by August 2020 (from 18,503 at end of 2019)
- Linking domains from 28 to 204 by November — the October 2020 PR launch was the inflection point
- Multi-language expansion: Spanish and Chinese versions of top-performing posts published with measurable traffic, before Deliverr had any localized teams
- Q4 2020 blog content portfolio: 79 posts contributed 218 first-touch CLTs (Connected Listing Tools; our marketing-attributable signup metric) over a 90-day window.
- Single blog post value at peak: $8,400 in CAC equivalent.
Discoverr 2020 was the year’s flagship event. Deliverr’s first virtual seller conference, two days (July 28–29), 6 sessions, 17 speakers, $9K total spend against a $20K forecast (55% under budget). 3,047 registrants, 1,241 attendees (41% live-attendance rate, well above the typical 25-30% B2B virtual benchmark). The unlock for the attendance number was random-giveaway promos for live attendees. The unlock for the budget was 10+ partner sponsors (Google, TikTok, Wish, Clearco, Gorgias, Pura Vida, AdKings, Kaspien, MarketplaceOps, Ritual Zero Proof) amplifying through their own audiences instead of us renting paid attention.
I recruited 17 speakers from named brands; Pura Vida Bracelets (Director of Acquisition Deirdre Kelly), TB12 (VP Product+Marketing Lauren Blanda), Glamnetic Founder,, Kaspien, Google Shopping, TikTok Head of Global Commerce Partnerships, Clearco Director of Channel Partnerships, and more for an event run by a then-Series-B startup.
The partner-co-promotion pattern, the speaker-recruitment-as-the-actual-work pattern, and the under-budget operating signature all became proposal phases in 2021.
2021: Transition
By mid-2021, Deliverr was 200 people. The Shopify acquisition was still a year out but the build-phase was over. I started transitioning out. June 1: consulting agreement signed (the first formal shift to a fractional role). Stock options exercised in May and June. LinkedIn farewell post in September.
But the second annual Discoverr conference still needed to happen, and the team asked me to come back as a freelancer to run it. By August, the engagement was ready to negotiate, and I sat down to write the proposal.
That’s the proposal this case study is about.
The August 2021 proposal
In August 2021, Deliverr asked me to come back as a freelancer to run Discoverr 2021 end-to-end. It ended up being a great benchmark for future projects!
- A 5-phase scope: Set up. Promotion. Coordination. Day of. Post-event. Each phase had explicit responsibilities listed underneath. You could read the proposal top to bottom and mentally simulate the entire engagement before signing it. No abstraction, marketing-deliverables-table, or vague “drive results” language. The phases mapped to a calendar.
- A “Needed from the team” section: Separate from the responsibilities table. Access to the webinar software. Confirmation of internal speakers. Confirmation of the proposed list of external speakers (with my suggested list of companies). Latest decks. Promotion budget. Reward structure. Permissions to edit Appcues and the website banner. Email scheduling and send. Pulled out as a checklist so the client committed to those inputs in writing alongside the retainer.
- A milestone payment schedule: Tied to the engagement phases, not to elapsed time.
- A multi-year-client bonus: “As a bonus for a multi-year client, I will continue monitoring metrics until October to report on the impact of the event.” Three years of FTE history converted into a small no-extra-cost gesture, written into the proposal itself.
- Extras: “Should you require training of an internal team member, for example to handle future events, this training fee can be discussed separately.” Named what could expand the scope without committing the base retainer to it. Offered further options rather than hard upsells.
The whole proposal was just two pages long, and became a reference for my future proposals for CMO clients.
A deeper look inside the phases
The five phases look like a project plan on the page. What’s actually happening inside each one is a specific operating posture I’d built up across earlier engagements — most of them from years before I wrote the proposal itself:
Set up and diagnostic first
Read the current state of the marketing function before prescribing actions. Years later at iDrive Logistics, the first thing the COO mentioned in his LinkedIn recommendation was *”she quickly gauged where we were and what needed to be done.”* If you prescribe before you diagnose, the work doesn’t match the actual situation. The “Set up” phase looks like landing pages and webinar registrations on the proposal page; what it actually is, is reading the room.
Promotion: Partner co-promotion before paid spend
The Discoverr 2020 inaugural conference (the one I’d run the year before this freelance return, while still FTE) hit 3,047 registrants at $9K against a $20K forecast — because 10+ partner sponsors amplified through their own audiences instead of us renting attention through paid ads. The 2021 return inherited that engine. In build-phase B2B where buyers need education to understand the offering, partner work beats paid acquisition every time. The “Promotion” phase is shaped by that lesson.
Coordination: Brief discipline and tooling fit
The contractor stack I bring to every engagement runs as a relay race. One disorganized link breaks the chain for everyone downstream. So the fast-fail trigger when I source new contractors isn’t raw skill — it’s whether they actually use the project management tools and follow the communication standards. The “Coordination” phase isn’t there to wrangle people; it’s there because the system has to survive each handoff.
Day of: Small operational levers
Random-giveaway promos for live attendees at Discoverr 2020 pushed live attendance from the typical 25–30% B2B virtual benchmark to 41% (1,241 of 3,047 registrants showed up live, instead of waiting for the recording). The “Day of” phase isn’t about running the day; it’s about having designed the right levers in ahead of time, so the day runs itself.
Post-event: The gesture that outlasts the engagement
The “extra month of metric monitoring” line in the proposal looks like a small no-extra-cost favor. Years later, Michael Krakaris — the co-founder I’d extended that gesture to — was one of the four people who wrote my Oxford EMBA recommendation letter. The other three: Brett Haskins at iDrive Logistics, Tom Wicky at MyFBAPrep, and Liz Downing (now Prospershow). Three of four recommenders are people whose engagements I designed using variants of this same proposal. The fifth phase is where engagements compound past their end date.
What the proposal turned into
I didn’t know at the time that I’d just written a repurposable template. Three years later, I started landing fractional CMO engagements across B2B eCommerce from different industries, different stages, and different scopes. Every proposal I wrote turned out to be a variant of the August 2021 Discoverr proposal. Phased scope. “Needed from the team” checklist. Milestone payment schedule. Extras as option, not default. A no-extra-cost gesture for relationships I valued. The structure flexes to fit the specifics of each engagement.
Three years of receipts:
MyFBAPrep (2021 – 2026): First marketing hire scope, sole marketer for five+ years. The 5-phase structure governed every brief, every quarterly plan, every content cycle. Inc 5000 multi-year (including #1 in logistics 2023 with 8,773% three-year growth), Amazon-Recommended FBA Prep Provider (1 of 7 forensically evaluated, July 2025), and 17% of inbound leads self-declaring AI search as their source by 2025 — the cumulative output of multi-surface authority work, not an AI-search sprint.
iDrive Logistics (2024 – present): Cold-prospect fractional CMO engagement. The COO found me via portfolio search and the proposal I sent him was a direct variant of the Discoverr 2021 template, adapted for build-from-zero scope. From zero website inbound to 20+ qualified leads per month in under a year. Two signed contracts from the first two inbound leads in the 40 days post-launch — the first inbound conversions in the company’s history.
I keep rewriting the same proposal because it keeps working. The structure makes the engagement legible as a project — which is what makes the fractional rate defensible to the founder reading it.
If you want the operations side of how the Discoverr 2021 engagement actually executed — speaker clearance protocols, last-minute change tolerance, what a 3-month recruitment runway buys you, why a 15-minute pre-session buffer matters — I wrote [a separate piece in October 2021](https://rachelandreago.com/deliverr-discoverr-conference-coordination/) covering exactly that. The conference scaled to 19 sessions and 40+ speakers across 10 hours of programming, up from 6 sessions and 17 speakers across 6 hours the year before. The operations writeup covers the *how* of that scale jump; this case study covers the *why* the engagement-design pattern held it together.
What this engagement says about how I work
Design engagements to survive transitions: I left Deliverr in September 2021. The Discoverr 2021 engagement worked out because the proposal made the project legible, even without my seat at the table. If your engagement structure assumes you’re sitting in the company, it won’t survive your exit.
Make the scope legible from page one: The proposal reads like a project-management artifact, not a sales pitch. Five phases, explicit responsibilities, input checklist, milestone payments. A founder reading it can mentally simulate the engagement before signing. That removes the kind of mid-engagement friction that sounds like “wait, I didn’t know we needed to do X” and kills fractional retainers.
The template is a reminder: The fractional model I use today was crafted to close a real engagement. Every variant since has been edits to the same proposal shape. I enjoy using it because it survived five years and shaped to four B2B-eCommerce sub-verticals before I gave it a name.
Where the playbook goes next
If you’re a co-founder or C-suite operator at a build-phase B2B eCommerce ops company and you’re trying to figure out what a fractional marketing engagement should look like before you hire one, reach out. I keep the roster small by design, especially now that I’m back in school for my EMBA, but the engagement-design conversation is one I’ll always make time for.