Ads by Jer Jeremy Chung × Pilot
Pilot.com — Paid Media Case Study Growth Marketing Lead · 20 Months Prepared for: CEO & CFO
Ads by Jer — case study — Pilot
Tenure · 20 months2021 — 2023
Paid media case study · written for the office of the CFO

Paid-sourced ARR: $3M → $25M in 20 months.

I rebuilt paid acquisition at Pilot.com into a portfolio governed by ROAS, payback, and pipeline-to-spend. Search did the heavy lifting at . Acquired Podcast was the contrarian win at 12×. Paid Social got capped at ~2×. Honest version below.

Paid-sourced ARR
8.3×
Budget managed
$5M+ /yr
The headline numbers
$22M
Net-new paid-sourced ARR added in 20 months.
9×
Paid Search ROAS — the engine. Drove 30–40% of total company ARR & pipeline in peak months.
12×
Top podcast partnership ROAS (Acquired). The contrarian bet that paid off.
~14mo
Blended CAC payback at exit. Inside the 18-month bar for SMB B2B fintech.
§ 01The Scorecard

Eight numbers, one page.

The view I walked finance through quarterly. Paid-sourced, campaign-attributed, reconciled to bookings monthly.

Paid-sourced ARR
$25.0M
▲ from $3.0M (8.3×)
Net-new ARR from paid channels at end of tenure.
Pipeline : Spend
8.6:1
▲ from 3.1:1
Pipeline generated for every $1 of paid spend.
Blended ROAS
4.7:1
▲ from 1.9:1
First-year ARR per dollar of spend, all channels blended.
CAC Payback
14mo
▼ from 26mo
Months to recover paid CAC on a gross-margin basis.
LTV : CAC
5.2×
▲ from 2.1×
36-month gross-margin LTV against paid CAC.
Blended CAC
$1.8k
▼ −42%
Held flat-to-down even as spend scaled 5×.
MQL → SAL
38%
▲ +14 pts
Lead-quality lift from segmented landing pages.
% of Co. ARR & Pipeline
30–40%
peak months · paid alone
Share of total company ARR & pipeline driven by paid in peak months.

End-of-tenure performance vs. baseline. Multi-touch attribution, finance-reconciled monthly.

§ 02The Curve

Compounding growth, not a sugar rush.

Three consecutive years of 3× YoY paid-sourced revenue. Search at the core, partner media compounding on top.

Paid-sourced ARR — quarter over quarter ($M)

20-month engagement
$25M $18M $11M $5M $3M Q0 Q1 Q2 Q3 Q4 Q5 Q6 Q7 Industry pace (2× over 20mo) $3.0M START $25.0M END · +$22M NET-NEW
Q0 — Baseline
$3.0M paid ARR · Search-only
Inflection — Q3
Newsletters & podcasts online
Q7 — Exit
$25.0M · 8.3× growth
§ 03Channels — the truth

Two clear winners. One clear loser.

Search and partner media carried the program. Paid Social never cleared 3× — capped, not killed. OOH was directional, not scalable.

Status
Channel
Spend
ROAS
Pipeline : Spend
Winner
Paid SearchGoogle & Bing — branded, non-branded, competitor
52%of budget
9.0×ROAS
14.8 : 1
Spend52%
ROAS9.0×
Pipe : Spend14.8 : 1
Winner
Newsletters & PodcastsAcquired Podcast + founder/finance newsletters
14%of budget
12.0×ROAS
14.2 : 1
Spend14%
ROAS12.0×
Pipe : Spend14.2 : 1
Winner
Retargeting & LookalikesTrust-building layer over Search demand
6%of budget
7.8×ROAS
8.4 : 1
Spend6%
ROAS7.8×
Pipe : Spend8.4 : 1
Mixed
Out-of-Home (SF)Validated by Gong call mentions, not direct attribution
6%of budget
2.1×direct ROAS
3.8 : 1 — indirect
Spend6%
ROAS2.1×
Pipe : Spend3.8 : 1
Underperformed
Paid SocialLinkedIn & Meta — capped, never cleared the bar
22%of budget
~2.0×ROAS
2.4 : 1 — below bar
Spend22%
ROAS~2.0×
Pipe : Spend2.4 : 1

Paid Social was capped — not killed — and kept for branded-search lift. Spend was reallocated monthly.

§ 04The Honest Reckoning

What worked, and what didn't.

A case study that only tells you the wins is selling you something.

What worked

Paid Search was the engine. Everything else compounded on top.

  • 9× ROAS · 52% of budget · 30–40% of co. ARR Paid Search The most reliable pipeline machine at Pilot. Branded and non-branded both cleared the bar. In peak months, Search alone drove 30–40% of total company ARR & pipeline.
  • 12× ROAS Acquired Podcast sponsorship The contrarian bet. Most B2B fintechs wouldn't touch audio in 2022. Best-performing line item by ROAS, full stop.
  • +14 pts MQL → SAL Segmented landing pages Different industries and company sizes saw different LPs. Lifted lead quality without raising CPL. Cleanest efficiency win of the engagement.
  • 7.8× ROAS Retargeting layer Cheapest, fastest-payback channel. Did not create demand — converted it.
  • Operating cadence Monthly spend reallocation Spend moved every month based on ROAS and payback. The discipline mattered more than any one tactic.

What didn't

Paid Social never cleared the bar. OOH attribution was thin.

  • ~2× ROAS · capped at 22% of spend Paid Social LinkedIn and Meta did not work for Pilot. Founder and CFO targeting on LinkedIn was expensive; Meta intent quality was poor for B2B fintech. We tried 12+ creative angles, three audience strategies, two LP redesigns. Never cleared 3×. Capped, not killed.
  • 2.1× direct ROAS OOH — directionally right, attribution weak Gong calls had real evidence prospects saw the boards. But direct attribution was thin and we couldn't justify scaling beyond an SF pilot. Honest call: brand investment, not performance.
  • First 6 months Slow creative cadence early Took a quarter longer than it should have to set up weekly creative testing. Lost months of Paid Social learnings before we hit our stride.
  • Quarter of delay Attribution debt at the start The first six months went into measurement and finance reconciliation — not new channels. Necessary, but it pushed channel diversification a quarter later than it should have been.
§ 05How I Operate

I don't wait for the dashboard. I run the dashboard.

Lagging metrics tell you what already happened. I run a layer of leading indicators — and a written prioritization rubric — to stay a step ahead.

I run a layer of predictive metrics — leading indicators that move 4–12 weeks before financials do — and a written prioritization rubric that decides where dollars and hours go. The job is to act on the signal, not narrate the lag.

Operating creed
01
Default to ownership.Orphaned numbers are mine until they're not.
02
Predict, then prove.Hypothesis + kill criterion, written, before dollars move.
03
Bias to action.A two-week test beats a six-week debate.
04
Cut losers fast.Capped Paid Social at month four. Doubled Search the same week.
05
Marketing is a P&L.Pipeline:spend, payback, LTV:CAC. Not impressions.
FW 01 / Predictive metrics

The leading indicators I watch every Monday.

By the time CAC and ROAS shift, the cause has been visible for weeks. These five signals move first. If any two slip in the same week, I rebalance spend before the monthly review — not after.

Branded search CTRleads category demand by ~6 wks
SQL→Opp velocity (median days)leads pipeline by ~4 wks
LP form-to-MQL conversion by segmentleads CAC by ~3 wks
Sales-rep “where did you hear about us”leads attribution by ~8 wks
Repeat-visit cohort depth (paid, 30d)leads payback by ~12 wks
FW 02 / Prioritization rubric

ICE, then a kill criterion. Written down or it doesn't ship.

Every test gets scored on Impact, Confidence, and Effort — then a written kill criterion before launch. If we don't know how we'd shut it down, we don't turn it on. Ruthless on what we say no to.

Score = (Impact × Confidence) / Effortthreshold > 6.0 to fund
Reversibility checktwo-way doors first
Pre-mortem & kill criterionwritten before spend
Time-to-signal budget14 days, then decide
No more than 3 active tests / channelavoid noise saturation
FW 03 / Weekly cadence

Tight feedback loops with sales, finance, and creative.

Marketing only compounds when the loops close. I run three standing meetings every week, each with a single decision output. No status updates — only reallocations.

Mon: spend reallocation w/ analyticsdecision: where the next $
Wed: lead-quality review w/ AE leadsdecision: which LP / segment kills
Fri: creative test readoutdecision: scale, iterate, kill
Monthly: CFO scorecarddecision: budget envelope
FW 04 / High-agency defaults

What I do when no one's asked me to.

The work that actually compounds is the work no one assigned. I default to picking up the orphaned number and running with it until it's fixed — then handing it back wrapped in a process.

Wrote Pilot's first marketing→finance reconno one asked
Built the segmented LP system end-to-enddesign, copy, dev, QA
Owned the Acquired Podcast bet personallycontrarian; 12× ROAS
Stood up weekly creative-test rubricclosed a quarter of debt
Ran the budget reforecast w/ FP&Amarketing as P&L partner

Prioritization in practice — H2 2022 at Pilot.

Live decisions · not retrofitted
Initiative
Hypothesis
Kill criterion
Outcome
FundedSegmented LPs by ICP
Match LP to industry & size will lift MQL→SAL by 10+ pts at flat CPL.
If MQL→SAL doesn't move +5 pts in 30 days, revert.
+14 pts MQL→SAL.Cleanest efficiency win of the engagement.
FundedAcquired Podcast sponsorship
Founder/CFO audience overlap is real; SOV in audio is cheap vs. LinkedIn.
If sourced pipeline < $750k after 90 days, don't renew.
12× ROAS.Best line item in the portfolio. Renewed.
CappedLinkedIn + Meta scaling
B2B fintech intent is too thin for paid social to clear 3× ROAS at scale.
If 12 creative iterations don't break 3× in 90 days, cap at 22%.
Held at ~2×.Capped — not killed. Reallocated $ to Search.
ShelvedOOH expansion past SF
SF pilot will produce attributable lift; expand to NYC if it does.
Direct attribution < 2× → brand budget only, no scale.
2.1× direct.Honest call: shelved past pilot. Real but unscalable.
§ 06CAC Compression

Blended CAC down ~46%. Payback inside 18 months.

Five levers, attacked in parallel. Capped the channels that would have given the gain back.

Before · month 0

Heavy paid social spend, undifferentiated LPs, monthly attribution lag.

Paid Social was 38% of budget at ~2× ROAS. One LP per campaign. Attribution closed mid-month — too late to act on. Spend reallocations were quarterly, not weekly.
Blended CAC
$1,840
Payback
26mo
LTV : CAC
2.4×
% paid pipeline
18%
After · exit

Search-led mix, segmented LPs, weekly reallocation, capped losers.

Search at 52% of budget at 9×. Eight segmented LPs across ICP × size. Daily attribution; Monday spend reallocation. Paid Social capped at 22%. OOH shelved past SF.
Blended CAC
$990
Payback
14mo
LTV : CAC
5.2×
% paid pipeline
42%

Where the $850 of CAC reduction came from.

Bridge from $1,840 → $990 blended. Each lever attributed to the change in blended CAC.
Starting blended CACMonth 0
$1,840
Search expansion + neg-keyword purgeLever 01
− $360
Segmented LPs by ICP × sizeLever 02
− $215
Paid Social cap (38% → 22% of budget)Lever 03
− $180
Acquired Podcast (incremental)Lever 04
− $115
Retargeting layer + bid automationLever 05
− $95
CPM inflation (industry headwind)Drag
+ $115
Ending blended CACExit
$990
$0$920$1,840
§ 07The Paid Media Playbook

The tactical moves that actually drove it.

The specific things I built inside Pilot's accounts — each tied to the CAC and ROAS gains above.

PLAY 01Search structure

Rebuilt the Google Ads account around ICP, not product.

Inherited a product-keyword account structure. Tore it down. Rebuilt around ICP segments (industry × size × pain) so bidding, copy, and LPs could be tuned per segment. Added a tight branded shell around defensive terms to lock down high-intent traffic at low CPC.

Impact− $360 CAC · 9× ROAS at 52% of budget
PLAY 02Search hygiene

Negative-keyword sweep + match-type discipline.

Audited 14 months of search-term reports. Built a 3,200-term negative-keyword list. Moved broad-match into phrase + exact wherever it was burning budget on bookkeeping/CPA generic terms. Wasted spend dropped within two weeks.

Impact~22% wasted-spend reduction in 14 days
PLAY 03LP system

Eight segmented LPs across ICP × company size.

One LP per campaign was costing us conversion rate. Built a templated system with eight LPs — four industries × SMB/MM — each with industry-specific social proof, pricing framing, and CTA. Shipped the whole system in five weeks with a single contractor.

Impact− $215 CAC · +14 pts MQL→SAL
PLAY 04Bidding

Smart Bidding with offline conversion imports.

Stock conversion signals were too noisy — form fills aren't equal. Wired offline conversion imports from the CRM so Google was bidding on SQLs and Opps, not raw leads. Switched to tCPA per segment with strict ceilings.

ImpactCPL down ~18%; SQL rate up ~12%
PLAY 05Retargeting

Retargeting layer with intent-tiered audiences.

Cheapest, fastest-payback channel — but only if the audiences are right. Built three tiers: pricing-page visitors (hot), feature-page visitors (warm), blog visitors (cold), each with its own creative and frequency cap. Killed the catch-all retargeting list.

Impact7.8× ROAS · − $95 blended CAC
PLAY 06Contrarian bet

Acquired Podcast sponsorship — the bet no one wanted.

B2B fintech wasn't sponsoring podcasts in 2022. Made the case the founder/CFO audience overlap was real and SOV was cheap. Owned the read scripts personally; A/B'd two creative angles; instrumented post-roll vanity URLs to attribute.

Impact12× ROAS · best line item by ROAS
PLAY 07Discipline

Capped Paid Social at month four — didn't kill it.

Twelve creative iterations, three audience strategies, two LP redesigns. LinkedIn + Meta never broke 3×. Made the call to cap at 22% rather than kill, to keep brand reach. The hard part was saying no to a channel everyone in B2B says you have to run.

Impact− $180 CAC · protected blended payback
PLAY 08Cadence

Monday spend reallocation — weekly, not quarterly.

Built a single-page reallocation report finance and I review every Monday: ROAS, payback, pipeline:spend by channel, week-over-week. Spend moves the same day. The discipline mattered more than any single tactic — it's what kept the gains compounding.

ImpactCompounded every other lever above
§ 08Funnel & Payback

Volume scaled 5×. Quality went up.

The hardest trick in B2B paid is scaling spend without diluting quality. Conversion rates rose as volume grew.

Funnel — exit state

Trailing 90 days at end of tenure. Deltas vs. baseline.
Leads · paid-sourced
100%
MQL · marketing-qualified
74% · ▲ +9 pts
SAL · sales-accepted
38% MQL→SAL · ▲ +14 pts
SQL · qualified opportunity
71% SAL→SQL · ▲ +6 pts
Closed-Won · paid-sourced ARR
62% SQL→Won

CAC payback — start to exit

Months to recover blended paid CAC. Lower is better.
Start26 mo
Mid-engagement19 mo
Exit14 mo · ✓
0 mo9 mo18 mo · target26 mo

Where the gain came from. Search efficiency improved as the partner channels came online. Paid Social was capped to keep it from dragging the blended payback.

§ 09Testimonials

From the leaders who ran the room.

From Pilot's CMO and Marketing Operations Manager.

"

Jer is a rare combination of deep performance marketing expertise and true business ownership, and is an asset to any executive team that cares about efficient, scalable growth. He has high agency, and works around the clock to make things happen.

At Pilot, he took full ownership of paid search and turned it into one of our most reliable and efficient pipeline engines, consistently meeting all KPIs; in several months he drove 30–40% of total company pipeline and ARR through branded and non-branded campaigns.

Since his time at Pilot, it has been great to see Jer continue to evolve his craft and expand his impact in the ecosystem. While I haven't managed him directly since then, it's clear from the companies he partners with and the reputation he has built that he's grown into a true paid media leader and agency owner. He brings the same rigor, ownership, and cross-functional mindset he demonstrated in-house, and it's no surprise to see him become a trusted partner for teams looking for both strategic guidance and hands-on execution.

RA
Rao Adavikolanu
CMO, Pilot
"

Jer has a unique blend of strategic vision, analytical prowess, and creativity that sets him apart in the growth marketing world. When we were working at Pilot, he immediately identified growth opportunities and crafted innovative strategies to achieve our targets.

In just 4 short months, Jer helped Pilot scale the performance marketing function from 0 to a 100. His ability to deep dive into analytics and extract insights helped us achieve visibility into the pipe to spend ratio and also experiment with different demand gen initiatives that helped grow and scale the business.

Jer is intelligent, humble and is great at making complex tasks easy to implement. He's the best growth partner I've worked with and I hope I get a chance to collaborate with him again in the future!

PT
Pavani Tatikola
Marketing Operations Manager, Pilot
§ 10The CFO Take

Six questions a CFO asks. Six clear answers.

No marketing language. The numbers a finance team needs to underwrite a paid program.

Q1Will it pay for itself?
14-month CAC payback at exit.
Down from 26 months at the start. Inside the 18-month bar most boards hold their growth orgs to.
Q2How efficient is each dollar?
Pipeline 8.6 : 1. ROAS 4.7 : 1.
Paid Search returned 9×. Acquired Podcast returned 12×. Paid Social was the drag at ~2×. The blend held because the winners were big enough to absorb the losers.
Q3Is the growth durable?
3× YoY for three straight years.
Five channels. No single point of failure. Search is the core; partner media is the multiplier. LTV : CAC closed at 5.2× — well above the 3× bar.
Q4Did volume cost us quality?
No. MQL → SAL up +14 pts.
Spend grew 5×. Lead quality rose at the same time. Segmented landing pages did the work. No sales-org pushback.
Q5What's the downside risk?
Worst channel capped at 22% of spend.
No single experiment ever exceeded ~10% of monthly budget. Paid Social underperformed, was capped, then absorbed. Risk managed at the portfolio level.
Q6What did this cost?
Mid-7-figure annual budget. $22M net-new ARR.
At conservative gross margin, the program paid for the entire growth org many times over.
Considering a similar engine?

Let's talk about your paid engine.

I now run Ads by Jer — a fractional growth practice running this same playbook for B2B fintech, AI, and enterprise SaaS. If your CFO is asking the same questions Pilot's was, I can help.

Or email jer@adsbyjer.com directly · adsbyjer.com