Patreon · Creator economy platform · Windows MDM displacing Microsoft Intune
RB2B pinged Slack: an IT Manager at Patreon was on our site. I ran a personalized double-tap cold call, LinkedIn connect, and cold email inside the hour. Reply in under five minutes. Booked call. Five to six weeks later Patreon was the logo that validated Swif — the proof point behind +200% growth, cash-flow positive, and a $100K raise at Pegasus Angel Accelerator on the way to a $3M round.
RB2B de-anonymized the visit and dropped it into Slack. I didn't wait for the form fill — I pushed the account into a same-hour, fully personalized sequence: two cold calls, a LinkedIn connect, and an email referencing exactly what they'd been reading.
Alyssa (IT Manager) brought three power users. Intune was clunky and their small team had no bandwidth to configure it properly. Offboarding through Allwhere was manual and disorganized — IT was physically walking to the mail room to ship and receive laptops.
I mapped upward to Jeff Chou, her Director, and pulled the evaluation into Slack — their preferred channel — so the whole buying group lived where the work happened. Two-week pilot, mutual action plan, dates owned on both sides.
Silence. Instead of nurturing into the void, I worked my other champions and learned she was on PTO — and that her birthday had just passed. A gift card and a human note restarted the deal in a day.
Quantified ROI against Intune admin hours and manual device logistics, became vendor of choice, and closed the Windows fleet. Their macOS fleet still runs on Kandji — that's the $15K expansion in flight.
“One intent signal, worked in under five minutes, became the logo that proved the category — and the growth story behind the raise.”
Alkami Technology · Digital banking SaaS · ~938 employees · NASDAQ: ALKT
Alkami had a strong marketing team and exactly one BDR — no structure, no tooling, no real outbound motion behind him. Marketing was traditional through and through. They handed me a list of target accounts and job titles. I enriched it, built the motion around it, and it worked.
Marketing was capable but entirely traditional — brand, events, content. Outbound sat on a single BDR with no structure, no sequencing discipline, and no tooling behind him. They gave me a list of target accounts and job titles and asked me to make it produce.
I enriched their account and title list — contact data, org structure, trigger events — then built the sequencing, channel mix, and messaging on top of it. Every “not right now” got documented into a timing-signal database.
When Alkami brought on a marketing lead, I synced with her proactively, learned her KPIs, and aligned outbound to fuel her pipeline goals — turning a potential blocker into an internal champion.
Results proved the model. $250K+ in pipeline generated, renewal secured, and a second team added — $50K total contract value, paid upfront, closed/won.
“Fuel into the fire.” Renewed $25K and added another team. That's what happens when the motion is built right.
The deal is won in the rooms I'm not in. My job is to make sure an army of champions walks into those rooms with better ammunition than anyone arguing against them.
Organizations now buy without the rep in the room. They talk about you when you're not there. So I don't sell to a meeting — I sell into the conversation that happens after it.
Nobody funds a product. They fund an initiative. I attach to the initiative that already has attention, budget gravity, and an executive who has to report on it.
There is always someone inside pushing for change and getting nowhere — usually more than one. I find them, test whether they'll push and whether they can reach power, then hand them the arsenal — the numbers, the language, the one-pager — so they can win the internal argument without me.
I don't pitch answers. I ask the questions that make the cost of doing nothing impossible to unsee, then quantify ROI and COI in the buyer's own numbers.
Taylor Hawkins, Sr. Systems Administrator, was the rebel. He wanted out of a dual-MDM setup buried under an MSP. I built him an executive summary in his language — situation, complication, recommendation, quantified — and he carried it up to his Director, then to Jacob Rosales, VP of Engineering. Closed-won.
Mixed Mac and PC fleet run through Jamf Pro for Macs, Casia for Windows, Drata for compliance, and ElectricAI as the MSP. Renewal on the calendar created the window.
Every deployment ran $1,000–$2,000 in fees, so the team simply stopped deploying software. That's not a tooling problem — it's a productivity tax with a dollar figure.
Unified device management across macOS, Windows, Linux, iOS and Android; silent Windows install via Azure; policy and patch automation; compliance center mapped to SOC 2 and ISO 27001; automated onboarding and offboarding with no physical handling.
Taylor pushed the summary to his Director, then to Jacob Rosales, VP of Engineering. The document did the multi-threading for me. $10K SaaS closed-won.
"If my champions can't win the argument without me in the room, I haven't done my job yet."
Six months nurturing a fast-growing tax incentive firm. A-team assembled, ROI quantified, CRO on the final pitch. Then a third person appeared — a silent partner who owned part of the company and called the shots. I had mapped the CEO and Co-Founder meticulously. I never validated the Economic Buyer. He killed a $100K deal in one call.
Team expanding, building their own software, momentum everywhere. I assembled my A-team — best copywriter, best team lead, best SDR callers — quantified ROI, and built the full presentation.
Highest-level alignment achieved on both sides. The deal felt as close as it had ever been.
A silent partner who quietly owned part of the company appeared on the call. He was never on my radar. He was the real Economic Buyer.
They renewed for one quarter — a small win. But the $100K was gone. I have never skipped Economic Buyer validation since.
Always validate the Economic Buyer. Before the pitch. Before the CRO call. Before month six.
Most reps know the playbook. Few execute it at every stage. This is where I'm different — and where the attainment comes from.
I map business architecture before I pitch anything — top-down or bottom-up. Problems, goals, process, place. Most of my discovery happens outside the call: org structure, initiatives, reporting lines, who actually owns the budget. I don't pitch until the map is built.
“What makes solving this important now versus six months ago?”
One champion is a single point of failure. I build a coalition and pressure-test every name in it: does this person push internally, and do they have access to power? If the answer is no on either, they're a friend — not a champion. Link chart analysis surfaces mobilizers, blockers, and anti-sponsors so I get to the Economic Buyer early.
“If they don't push and can't reach power, they're not a champion.”
I quantify hard ROI (time savings, FTE offset, revenue), strategic ROI (priority alignment), and COI — the cost of a 30, 60, or 90-day delay. When inaction has a price tag, the conversation moves from budget to urgency.
“The cost of doing nothing is always higher than the cost of the tool.”
I don't run a single methodology dogmatically. MEDDPICC qualifies, GAP uncovers, Challenger teaches, and Command the Message gives the champion the language. Together they make the forecast honest.
The engineering isn't the product — it's the leverage. Signal becomes a system, the system produces conversations, and the seller closes them. Three links in one chain.
Benchmarks from sequenced cold outbound across mid-market and Series A motions — measured on sends, not on a curated sample.
"I build the system so the pipeline is never the excuse. Then I go close it."
Proof has the receipts — Apollo Labs and Swif.ai end to end, CRM screenshots, and recorded walkthroughs.