Ecommerce Playbook: Numbers, Struggles & Growth

Sales tax feels simple—until you hit nexus.
In this episode, Ryan Pinkham (VP of Go-to-Market at TaxCloud) breaks down why sales tax gets complex fast for growing ecommerce brands, what happens when you cross nexus thresholds in new states, and how ignoring compliance can turn into a painful (and expensive) distraction.
We cover:
What sales tax nexus actually means for ecommerce

The three “buckets” of brands (doing nothing, unhappy with current tools, or knowingly delaying)

Why sales tax is a year-round operational load

How modern brands approach checkout tax vs. filing/registration

The Streamlined Sales Tax (SST) program and why 24 states matter

A simple start-of-year checklist to get compliant and reduce risk

If you had a strong Q4 and expanded into new states, this is your sign to do a quick nexus and tooling review..
Show Notes:
TaxCloud has you covered: https://taxcloud.com/thread/

Explore the PROPHIT System: http://prophitsystem.com

The Ecommerce Playbook mailbag is open — email us at [email protected] to ask us any questions you might have

Acquisition is getting tighter! In this episode, we flip the script and talk about the lever most brands under-invest in: retention + lifecycle marketing.
Taylor is joined by Jennifer Peters, Director of DTC, MarTech & Digital Compliance at OLLY (a Unilever brand), to break down how they think about keeping customers coming back when the brand is sold everywhere — from Target and Walmart to their own DTC site.
We get into what retention really means beyond “subscription,” how to message customers when you don’t want to channel-shift them, and how OLLY is using loyalty (including receipt scanning) to better understand in-store shoppers.
What you’ll learn:
How OLLY drives retention across DTC + retail

Email vs SMS strategy, plus segmentation that prevents “list blasting”

Using loyalty + receipt scanning to understand in-store shoppers

Setting smarter KPIs for promos, launches, and content

Why they chose Attentive, how they handled ESP migration, and where AI actually helps

The first retention moves: audit flows, refresh creative, nail the basics

If you’re running ecommerce for a consumable, CPG, or multi-channel brand, this is a must-watch for building a retention engine that actually scales.
Show Notes:
See how Attentive helps connect people and the brands they love.: https://bit.ly/4ag8oEJ

Explore the PROPHIT System: http://prophitsystem.com

The Ecommerce Playbook mailbag is open — email us at [email protected] to ask us any questions you might have

In this episode, Richard and Luke unpack a pattern they couldn’t ignore after running 224 sales call transcripts through an LLM:
The #1 issue mid-market ecommerce brands face isn’t that performance is down… it’s that they don’t know why performance is happening.
And when you don’t trust the numbers, you can’t trust the decisions.
Luke walks through a painfully familiar weekly business review scenario—multiple agencies, multiple dashboards, multiple “versions of the truth”—where 80% of the meeting is spent trying to figure out what’s actually going on, and almost none of it translates into confident action.
What you’ll learn in this episode:
Why brands don’t hire help because results are bad—they hire because clarity is missing

The hidden cost of “dashboard chaos” (and why more stakeholders often makes it worse)

The 3-step framework to go from confusion → clarity → action:

Why incrementality (geo holdouts) is the gold standard when ROAS debates never end

How to sanity-check your “real-time” metrics against your closed P&L (and what variance is acceptable)

They also tease what they’ve been building to solve this problem end-to-end: a higher-capacity operator role designed to reduce complexity and speed up decisions—so your team spends less time arguing about numbers and more time changing outcomes.
If you’re leading growth at a brand in the $10M–$100M range and your team spends more time debating performance than improving it, this one will hit home.
Show Notes:
Axon is offering $5K ad credit when you spend $5K. Go to https://axon.ai/en/ctc to set up your first campaign.

Explore the PROPHIT System: http://prophitsystem.com

The Ecommerce Playbook mailbag is open — email us at [email protected] to ask us any questions you might have

Scaling a DTC brand from $1M → $10M isn’t about finding more “hacks,” it’s about focusing on the right growth lever at the right revenue stage.
In this episode, Richard and Joy, break down a practical “one move per stage” roadmap for scaling through seven figures into eight.
What you’ll learn in this video
$1M → $2M: Why creative volume is the unlock (and why the benchmark is ~100 ads/month)

$2M → $3M: Build a marketing calendar (one marketing moment per month) to create “reasons to buy” beyond evergreen

$3M → $4M: The stage where brands stagnate most: offer market fit + offer testing (and why it’s so industry-dependent)

$4M → $5M: Creative again—but at a different level (think 100 ads/week)

$5M → $6M: Product development for LTV (front-end vs back-end products, subscription angles, upsell paths)

$6M → $7M: When “tactics” finally matter—international expansion, audience expansion, email, CS, and other incremental edges

$7M → $8M: Why media buying becomes bespoke (your account structure should reflect what’s working: promos, whitelisting, LP testing, subscription, etc.)

$10M+: The real unlock becomes people—why one A-player operator can outperform 10 average hires

The big takeaway
Most brands don’t need more noise—they need ruthless prioritization. The fastest path to $10M is doing the right thing for your stage, deeply, before moving on.
Show Notes:
See how Attentive helps connect people and the brands they love.: https://bit.ly/4ag8oEJ

Explore the PROPHIT System: http://prophitsystem.com

The Ecommerce Playbook mailbag is open — email us at [email protected] to ask us any questions you might have

In this episode, Richard and Luke break down the system we use to help 8-figure ecommerce brands stop guessing and start making confident decisions about budget, creative, and channel investment.
They walk through the three core models that answer the questions every operator wrestles with:
How much should we actually spend right now?

How much creative do we need to support that spend?

Which channels should we test next — and why?

You’ll learn how to spot when additional ad spend becomes a bad trade, how to plan creative volume around real marketing moments (not vibes), and how to prioritize incrementality testing based on potential revenue impact — not opinion or politics.
If your team would answer these questions differently depending on who you ask, this episode is for you.
What we cover:
How to identify when ad spend stops being efficient

The Spending Power Model and how it sets real budget caps

How creative volume directly affects performance and efficiency

A practical framework for planning moment-based vs evergreen creative

How to prioritize channel tests using incrementality ranges

Why “waiting for perfect data” is often more dangerous than acting
If you’re running or advising an 8-figure ecommerce brand and want a clearer way to allocate budget, plan creative, and make smarter growth decisions — this episode lays out the playbook.

Show Notes:
Get Dataships' free A/B test: https://www.dataships.io/demo

Explore the PROPHIT System: http://prophitsystem.com

The Ecommerce Playbook mailbag is open — email us at [email protected] to ask us any questions you might have