Wil Cleaveland

Growth & Lifecycle Marketer | $10M+ in funnel revenue | AI-fluent

Daily email and SMS campaigns, funnel copy, CRO, and the AI systems that ship it all faster.

Resume

Summary

Growth and lifecycle marketer with 10+ years of direct-response experience, turning cold prospects into paying customers — $10M+ in tracked sales funnel revenue across DTC ecommerce, B2B/B2G SaaS, and financial/info-product offers. A self-directed operator who thrives where reward tracks effort, and who wins in skeptical, high-trust markets that punish generic pitches. Built and led copy teams of up to 8; now also directs AI to ship production marketing infrastructure.

Skills

Direct-response copywriting · Email & SMS marketing · List management & deliverability · Conversion rate optimization (CRO) · Sales funnel copy · Lifecycle automation · Sales enablement & B2B/SAAS content · Offer construction · Team leadership

Stack: Maropost · Attentive · Shopify · GoHighLevel · Claude / Claude Code · Python (AI-paired) · Adobe Creative Suite

AI-Augmented Marketing Tool Builds

Marketing software I've directed AI to build, ship, and operate. The first is public with a live demo you can try right now; the rest run the daily email program of a $5M+/yr direct-response brand, replacing what would have required a developer hire.

Winner-Grounded Copy Engine

A fresh-angle generator that works like a DR marketer, not like ChatGPT with a marketing prompt. Point it at a live sales page: it reads the brand's voice, offer, and proof, extracts the mechanisms behind copy that already converted (paste a winner, screenshot one, or pull a competitor's currently-running Meta ads), generates a stress-tested matrix of fresh angles, then expands survivors into full emails or Meta ads. Try the live demo →

Tools: Next.js · Claude · Meta Ad Library · Claude Code

UGAR Campaign System

A Python pipeline that authors, audits, and pushes daily Maropost campaigns across multiple formats (Daily Style, Editorial PM, Daily 11am, and more). Dry-run mode for safe drafting; --execute for production push. Pre-flight auditor catches stale logos, body/text mismatches, broken affiliate links, and missing required elements before any send.

Tools: Python · Maropost API · Claude Code

Daily Hard-Bounce Suppression

Scheduled, unattended task that runs every day: discovers all sent campaigns in the window, pulls bounce reports via the Maropost API, identifies hard bounces and mailbox-full SMTP codes, and updates the active suppression list. Reduces ESP costs by removing bad addresses before the next send and protects sender reputation.

Tools: Python · Maropost API · macOS launchd / Claude scheduled tasks

Click-Tracking Slug Infrastructure

Custom redirect domain (mail.<brand>.com/<slug>) that replaces long affiliate URLs in campaign body with branded short links. Server-side PHP redirector reads a client-uploaded mapping file and forwards to the affiliate URL with all tracking parameters intact (aff_sub, click_id, etc.). Reduces body clutter, improves deliverability, and gives the brand consistent click-tracking surface.

Tools: PHP redirector · JSON mapping · Python author-side integration · Claude Code

Cross-Platform API Integrations

In-progress: a Konnektive CRM ⇄ Ottertext SMS tag-mapping layer. Customer segments defined in Konnektive (purchase history, tags, lifecycle stage) flow into Ottertext campaigns automatically — removing the manual list-pull step from the SMS send workflow. Foundation for unifying email + SMS audience targeting under one CRM-driven source of truth.

Tools: Python · Konnektive API · Ottertext API · Claude Code

Experience

Growth & Lifecycle Marketer — Patriot Training Center
Jul 2025 – Present
  • Closed ~70% of cold opt-in phone leads (75–100 calls), converting a discounted intro-class offer into onsite lifetime-membership sales — a low-ticket-to-high-ticket funnel.
  • Direct-response marketing for a $5M+/yr boutique self-defense training brand — own email, SMS, funnel optimization, list hygiene, and CRO.
  • Manage email + SMS promotional calendars across both internal and affiliate offers; reduce Maropost ESP costs via in-depth list hygiene.
  • Direct AI-augmented Python tooling for the email program (see AI-Augmented Marketing Operations above).
  • Engineer GoHighLevel automation workflows for inbound campaigns; optimize landing pages and funnels for cold traffic alongside business founder.
Chief Copywriter & Internal Media Manager — Sicuro Brands
Jul 2020 – Jul 2025
  • Owned all messaging and copy for three DTC ecommerce brands — VNSH Holster, Pain Safari, and Modern Needs Survival.
  • $10M+ in lifetime sales funnel revenue — VSLs, advertorials, order forms, upsells, downsells.
  • Maintained $50k+/week sustained email revenue from daily campaigns across brand lists.
  • Launched and scaled SMS program from zero to $20k+/week in revenue.
  • Ran CRO across funnels to elevate AOV and maintain profitability on cold traffic; analyzed COGS to construct new offers and improve live ones.
SAAS Marketing Writer — Nicus Software
Feb 2019 – Jun 2020
  • Built the company's #1 gated lead-gen asset by total leads (the ITFM/TBM Maturity Guide) for CIOs, CFOs, and IT Finance leaders at Fortune 500 companies and major government agencies.
  • Authored four published customer case studies — Visa, City of Seattle, American Family, and a major State Agency — through direct conferral with each customer's IT/finance leadership.
  • Maintained sales enablement collateral across the product line; authored BDR outreach scripts for phone, email, and video that the sales team actively used and iterated.
Direct-Response Copywriter — Independent Consultant
Apr 2016 – Feb 2019
  • Scaled email revenue to $300k/month for a survival/tactical client as copy team chief and list manager.
  • Wrote lead-gen advertorials for a financial direct-response client competing against Lending Tree and Eloan.
  • Consulted with biz-op direct-response businesses on increasing internal list revenue.

Education

Bachelor of Arts, Communication Studies — Roanoke College · 2013

Testimonials

“Frankly, one of the best hires that we’ve had… he’s just one of those people you don’t have to explain things to twice. He just gets it.”

— Caleb Osborne, Patriot Training Center


“Going on seven years now, I don’t think there’s anybody better when it comes to writing front-end copy, email copy, and even SMS copy… I’d hire him all day, over and over again.”

— Adam Lantelme, Sicuro Brands


“Wil has been very effective at maximizing revenue from our internal lists and generating winning funnel copy for all our brands — in both good times and bad.

In a niche where we’re constantly facing challenges to consistently scale on cold traffic, Wil’s performance is one constant we’ve been extremely thankful to count on!

Nathan Hopkins

— Nathan Hopkins, Sicuro Brands


Marketing in the ITFM/TBM space is uniquely difficult. Our buyers — CIOs, CFOs, and IT Finance leaders at Fortune 500 companies and major government agencies — are sophisticated and skeptical. They’ve heard every vendor pitch, can spot generic copy from a mile away, and have no patience for content that doesn’t speak intelligently to their problems.

When we engaged Wil, he had zero background in IT Financial Management. He’d never built a cost model, never run a chargeback program, never sat in on a quarterly IT budget defense. Most writers could never bridge that gap.

Wil ramped from zero to SME-level in a matter of weeks — producing collateral that read like the work of a 10-year ITFM practitioner, not a copywriter learning the acronyms.

He tactfully stoked our buyers’ complex pain points, in their own language, and consistently drew a sharp line from that pain to our solutions. Our sales team had collateral they actually wanted to share with prospects, and prospects engaged with it.

If you’re in a technical or specialist market and you’re worried that no outside writer will ever really ‘get it’ — Wil is the exception.


“As a guy who built an affiliate company, solely through email, from $0 to $300,000 every month, if I could choose 1 guy to do it again with from scratch. 1 no nonsense writer. 1 entrepreneur to create compelling email, converting sales copy and day 1 profitable product funnels that can scale.

I’d choose Wil because he was with me and built it to those staggering numbers along side me.

There are just not that many people that have written, tested, and analyzed the amount of copy Wil has.

There are even fewer who have critiqued thousands of cold traffic emails, and made them work, while leading a team of 8 writers to do the same.

Frankly, copy is a key component that makes the rain inside any business. Most can’t produce it. Less can analyze it. Less can teach it. Less can grow a profit line with it, day in and day out.

Wil does all of that.

Period.”

Lou Cozzolino

— Lou Cozzolino, Lone Survivalist


“I’ve outsourced to other writers here and there, but Wil is my go-to guy when I need to outsource copy.

He has excellent research skills. He’s self-motivated. He hits deadlines. And he writes damn good copy.

I can toss him an idea and let him run with it without ever worrying if we’re on the same page. He knows how to take feedback. He asks the right questions. Overall, he just “gets it.”

His abilities are quickly eclipsing “up-and-comer” status, and I strongly recommend you work with him. (In fact, I often send him referrals.)

Just please don’t send him too much work… I’d like to keep working with Wil for a long time. ;-)”

Ryan Healy

— Ryan Healy, Upsender


I’m super impressed with Wil’s ability to deliver quality copy on time and on budget. He is easy to work, gets things right the first time (e.g. doesn’t require handholding or endless revisions) and will surely be an asset to anyone seeking a competent and reliable copywriter.


“Wil is an incredible copywriter.

He’s able to immediately look at any copy, trim the fluff, and get the prospect to take action.

His ability to whip up control-quality emails on the spot always amazes me.

But he also knows how to lead and manage.

He’s quick to celebrate team wins. While also happy to spend time helping and teaching others how to make their copy stronger and tighter.

You can tell he’s driven from a place of helping everyone succeed. No ego.

I attribute a lot of my current copywriting skills to Wil’s patience and coaching.

It’s been a pleasure working with Wil, and wouldn’t hesitate to do so again in the future.”

James Wilder

— James Wilder, Advertising Hustle


Wil has been an integral part of building the Marketing Team at Nicus. In a challenging industry with limited resources, Wil crafted exceptional content to generate demand for Nicus’s solutions. He has been a fast learner, and his intellectual curiosity will continue to serve him well throughout his career. He was properly nicknamed the “Word Man” at Nicus for spinning any context into sweet lullaby. I’d not only recommend him; I’d hire him time and time again.


Wil is a pleasure to work with. He’s prompt and professional. Writing for different industries is always a challenge, but he’s been able to quickly adapt to each client’s unique voice and industry jargon and always delivers great copy that requires minimal (if any) editing. I wouldn’t think twice about referring him or bringing him on-board for another project.


“I was referred to Wil by Ryan Healy, whose schedule was too full to accommodate our landing page project. Wil had just started freelancing full-time, so his portfolio wasn’t quite as filled out as the other copywriters we looked at. But when we got back the first draft of our copy, we knew we’d made the right choice.

His process was seamless, and he got the tone and voice for our audience almost perfect right out of the gate. He even found a great clinical study for an ingredient in our product that we had yet to discover ourselves. Then he integrated it right into the copy.

We’re anxiously counting down till launch day so we can test it out!”

Ben Steuart

— Ben Steuart, Steuart's Natural Health


I had the pleasure of working with Wil and highly recommend him. He is an extremely talented marketing writer with the ability to produce meaningful content with just a few conversations with subject matter experts. He has a strong work ethic and a desire to learn new things. I was impressed with how quickly he was able to understand and navigate a fairly technical topic like IT Financial Management. Beyond all of this he was a great team mate, always helpful and friendly, with an infectious positive attitude! Your organization would be lucky to have Wil!

Work Samples

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Sicuro Abandon Cart Journeys

A collection of abandon-cart email sequences I wrote for Sicuro Brands. Six sequences across the VNSH and Modern Needs portfolios — layering courtesy reminder → price-increase urgency → discount → reservation-expiry to win back the cart. Click any email below to read the copy.

- 6 journeys / 21 emails
- VNSH and Modern Needs offers
- Layered urgency, scarcity, and discount logic

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Modern Needs Survival Sauna Bag

Cold traffic on this offer only became profitable after AOV work — a multi-quantity pricing structure with a free-bonus threshold at 4+ units. A good example of fixing offer economics instead of just rewriting copy.

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Modern Needs Ready Filter

A value-priced front-end offer in a crowded category — it converted well on cold traffic, and I drove solid performance on the back-end of the funnel.

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Pain Safari XL Shockwave

A personal-security offer with strong built-in demonstration appeal. The funnel leaned into show-don't-tell product proof, which kept conversion high across the email list.

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Pain Safari Shockwave Mini

An internal-list offer that has stayed a consistent winner for over a year — sustained by fresh angles, seasonal hooks, and disciplined list rotation rather than cold-traffic spend.

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Advanced Cost Transparency — Datasheet

Premium-tier product sheet for Nicus's Advanced Cost Transparency module. Adds service & application TCO, public cloud integrations, business capability views, and the bill of IT (showback or chargeback) on top of the core cost modeling engine.

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Nicus Planning — Datasheet

Datasheet for the Nicus Planning module — the multi-currency, multi-year budgeting and forecasting tool. Highlights what-if scenarios, governance views (run/grow/transform), automated variance analysis, and the audit trail features finance teams need to defend their numbers.

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IT Cost Transparency — Datasheet

Datasheet for the core IT Cost Transparency module. Walks through how Nicus's cost modeling engine establishes fully-burdened cost structures, integrates with TBM taxonomies, and gives technology leaders the data to rationalize spend and benchmark against peers.

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Public Sector Bill of IT — Datasheet

Product data sheet for Nicus's Public Sector Bill of IT solution — covering automated invoicing, dispute and approval workflows, multi-fund tracking, and the chargeback mechanics that public agencies need to satisfy compliance and audit requirements.

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Nicus Blog Posts (30+)

A multi-year run of blog content for Nicus covering cost modeling pitfalls, chargeback strategy, ITFM/TBM program design, CIO-CFO alignment, recession playbooks for IT, and more. Each piece is linked below — most are still live on nicus.com.

- 30+ live posts
- Audience: CIOs, IT Finance leaders, TBM practitioners
- Mix of how-to, framework, and POV pieces

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ITFM/TBM Program Maturity Guide — eBook

An eBook framing the ITFM/TBM program maturity model across four dimensions — People, Process, Technology, and Data. Built to give IT Finance buyers a shared vocabulary for diagnosing their current state and mapping a credible path forward.

- 4-dimension maturity framework
- Designed for sales-enablement and BOFU demand gen
- Each section anchored to a real customer pattern

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State of Arizona Case Study

Long-form case study about Arizona's enterprise IT transformation under the Arizona Management System initiative — turning the state into a model of how showback and chargeback can reshape government IT economics.

- 35% overhead reduction with showback and chargeback
- 10,000 hours saved (~$480k, ~5 FTEs)
- $16.6M reinvested in enterprise services
- 25% YoY improvement in billing accuracy

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State Technology Agency Case Study

Public-sector case study about a state technology agency wrestling a $60M+ budget across 39 consuming agencies — and how a purpose-built cost modeling platform replaced an error-prone mix of Excel and a stand-alone allocation tool.

- $60M+ annual IT budget
- 39 separate consuming agencies
- Government-mandated double step-down reporting handled with built-in workflows

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Fortune 500 Insurance Case Study

Anonymized Fortune 500 insurance case study about a $70M annual IT budget trapped in spreadsheets — and the transformation that followed once IT Finance had a defensible source of truth.

- 33% reduction in non-labor planning effort
- 2,000 hours reclaimed annually
- 8 weeks taken out of the planning schedule

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A Practitioner's Guide to Cost Modeling — eBook

Long-form practitioner's guide to IT cost modeling — the kind of high-investment content piece that establishes thought leadership and drives demand-gen pipeline. Eleven sections covering what an effective model looks like, how to build and defend one, and the tangible business outcomes it unlocks.

- 11 sections / ~20 pages
- Used as a lead magnet across paid and organic channels
- Co-developed with Nicus subject matter experts

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Visa Customer Snapshot

Customer snapshot featuring Visa Inc. — a global payments giant managing $1.4B in annual IT spend. They ripped out Apptio in favor of Nicus in 30 days and reduced cost model run times from 13–16 hours down to 90 seconds.

- $1.4B annual IT spend managed in Nicus
- Apptio replaced in 30 days
- Cost model runs dropped from 13+ hours to 90 seconds

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Lifeway Customer Snapshot

A short-form customer snapshot showing how Lifeway moved $35M of annual IT spend off spreadsheets and into Nicus in just 60 days — accelerating planning cycles and freeing leadership to make spend decisions in real time.

- $35M annual IT spend managed in Nicus
- 2 modules in production in 60 days
- Revised spend plans socialized in real time

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City of Seattle Case Study

Co-developed this customer story documenting how the City of Seattle consolidated 29 separate IT shops into one centralized organization, replaced a dozen linked Excel spreadsheets, and won back thousands of analyst hours per year.

- Consolidated 29 IT shops into one
- 3,000 analyst hours saved annually
- Mid-year budget changes cut from weeks to a day

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American Family Insurance Case Study

Wrote this Fortune 500 case study chronicling how American Family Insurance partnered IT and Corporate Finance to gain cross-organizational cost transparency across 25 operating divisions and 2,600 agents — and stopped guessing about IT spend.

- Cross-organizational IT cost transparency
- Reduced staff hours on TCO studies
- Supported new chargeback methodology

Browse the complete work archive →