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[Company Name]:

Preliminary Content
Strategy Overview

The following roadmap is a preliminary strategy: an overview of how most

engagements are structured. Adaptations and notes specific to [company]
will be marked in red.

Our first step will be to establish three objectives from which to create key
results (OKRs). These do not need to be final or polished, just starting
points to understand your overarching aims.

Objectives are broad descriptions of your most pressing and important goals.
They should be qualitative statements:

● Short

● Memorable

● And, motivational

Key results, in contrast, are quantitative metrics we’ll use to monitor


● Measurable

● Time-bound

● And, above all, actionable

Objective 1

[If you’d like to, please fill in]

Objective 2

[If you’d like to, please fill in]

Objective 3

[If you’d like to, please fill in]


Typical three-to-six month engagements center on the following stages …

Stage 1: Positioning
Weeks 1-3
The majority of B2B organizations — particularly SaaS companies — already
have a wealth of data, existing content, marketing collateral, and customer
insights. Rarely, however, are those resources consolidated into a
comprehensive framework that’s actionable and accessible across

Rarer still are organizations who leverage their resources

systematically across the funnel in conjunction with their
product’s own metrics.
Surfacing these resources — through (1) a shared “content bank” (gathered by
the organization one month prior to start date), (2) stakeholder interviews,
and (3) analytics — will naturally reshape this overview and be a matter of
first importance.

In addition to collecting and reviewing existing collateral, we’ll examine:

1. Top features (product usage) of “sticky” customers

Growth hinges on product-market fit; and product-market fit arises from a

clear understanding of a SaaS’s critical events (also known as the “aha
moments”). These are in-product actions that correlate with (1) retention, (2)
customer success and (3) the product’s core value proposition.

In opposition to B2C growth strategies — where a single tipping point is

emphasized — sticky B2B customers are characterized by a cluster of
features: ~4-10 per segment.


Orienting your strategy first and foremost towards retention not only
anchors it in customer lifetime value (CLTV) … it also creates a feedback
loop between:

(1) Product-market fit

(2) Quantifiable customer success

(3) The product’s core value proposition

(4) Qualitative “hells and heavens” (see, Personas)

(5) Content creation, deliverables, and the strategy itself


2. Current funnel, lead-gen tech stack, and best-performing

marketing materials

Benchmarking always proceeds strategy. To assess the current funnel, we’ll

first identify the leading product-entry point(s):

● Trials started

● Demos completed

● Appointments set, etc.

We’ll also determine the characteristics of a marketing qualified lead (MQL)

and a sales accepted or qualified (SAL/SQL).

Then, we’ll set existing week-over-week baselines (content analytics) for:

● Traffic and sources

● Visitor to lead1 conversion rate (CVR) from …

○ Generic opt-ins

○ Content-specific opt-ins

● Product-entry conversion rates from …

○ Visitors: direct and assisted

○ Leads: general email list(s)

○ Marketing or sales qualified leads (MQLs/SQLs)

○ CVRs to paying customers by segment

1 Lead is a tricky term in B2B; for now, we’ll simply define it as visitor who “opts in” to receive
marketing (i.e., joins an email list) and disqualifies themselves as either a MQL or SQL based on their
answers during sign-up



Sample Google Data Studio dashboard to measure and optimize product-entry (new trials), churn (new
cancellations), and paying customers (new customers)

This process reveals (1) where an organization is bereft of data, (2) what’s
already working (and ought to be replicated), and (3) what isn’t.

Moreover, it will be a linchpin in measuring future success.

Examining the tech stack is equally illuminating, particularly as it applies to
internal chokepoints: the death of good content intentions — the death of all
good marketing intentions — are unnecessary or misaligned dependencies.
Chiefly, design and development.

3. Competitive summary of major alternatives: “Where our product

wins. And, where we lose.”


● Collect, finalize, share, and provide team-wide usability guidance for
the Content Bank (for a preview of what the initial gathering entails:
Content Bank Instructions and ToC). Normally, these are built within a
company’s own Google Drive and require login access to all applicable

Stage 2: Personas
Weeks 3-4
1. Develop at least three personas organized by role (e.g., job title)

2. Solidify product-fit characteristics for each persona based on (1)

business type, vertical, or industry; (2) technological complexity; and
(3) revenue ranges

3. Root each persona in a visceral description of their “hells” — what do

they hate about (1) themselves, (2) their business, and (3) the current
product landscape — and “heavens” — what do they long for (hell
inverted). As a guide, the 20 “Finding Their Hell” questions, which are
included at the end of this PDF.

● Complete at least three personas to integrate into the Pillars below
(namely, strategy and marketing calendar)


Sample persona


Stage 3: Pillars
Weeks ~5 and Ongoing
A successful B2B content strategy has one allegiance: the funnel, the whole
funnel, and nothing but the funnel.

1. Inbound acquisition

(a) Identify 10-15 “ground zero” keywords tied to specific product features

While keyword research is central to driving qualified organic traffic … it is

perhaps more vital as an exploratory tool for unearthing and prioritizing
marketing efforts as a whole.

A brand’s content — be it digital or physical — must (1) have a validated

audience in search of a solution and (2) align with that brand’s product-
market fit.
As such, ground zero keywords are more than keywords. They are
centers of gravity around which marketing orbits.



Sample Rankings Overview of client dashboard to illustrate search volumes for ground zero keywords
(blue column: client’s rankings after ~9 months; red column: top competitor)

By way of execution: consolidate and create 1-2 pillar pages per month —
along with content-prompted CTAs for gated assets — to (1) drive organic
and paid leads, (2) establish the written backbone of email nurture
sequences, webinars, short-form content, etc., and (3) serve as models for
long-term (in-house) content creation.

For mid-price point SaaSs — especially those where trials and onboarding are
integral to the purchase process — as well as for high-price point SaaS —
where sales teams are essential to the deal process — that second point
deserves repeating:


Establish the written backbone of email nurture sequences,

webinars, short-form content, etc.
All too often, lead nurturing falls into one of two extremes: (1) too aggressive
— immediately sending blanket “buy now” emails — or (2) too passive —
dumping leads into the purgatory of “our blog newsletter.”

(b) Identify ~25-100 “priority one” and “priority two” keywords for a
quarterly marketing calendar:

● High-volume search terms for awareness and thought leadership (top

of funnel)

● Low-volume, high-purchase intent keywords for direct-to-product

entry (middle and bottom of funnel)

Sample Keyword Research on “facebook ads” to group similar keywords by “Seed terms or content
target clusters” as well as stage of funnel (F), purchase intent (G), and search intent (H)


2. Sales enablement

Integrate a regular cadence — dependent on customer availability and

internal resources — of case studies for (1) MoF and BoF content through
email and retargeting and (2) to seed real data, real examples, and real use
cases throughout content creation.

Siloing content — high-volume top of funnel (ToF) and middle of funnel (MoF)
from low-volume bottom of funnel (BoF) — guts content of proprietary data
that proves success.

Seeding real data, real examples, and real use cases throughout content
creation (i.e., stacking traditionally BoF content — case studies — into ToF
and MoF content) enables all content to sell without selling.

3. Product marketing

Overlay the above strategy and calendar with product highlights: i.e., detailed
use cases backed by customer data (when possible) of current features and
upcoming releases.

● Keyword lists and current rankings

○ Ground zero: 10-15

○ Priority 1: 25-50

○ Priority 2: 50-100

○ Organized by clusters, state of funnel, purchase intent, search

intent, volume, and content types

● Pillar pages 1-2 and content upgrade (gated for lead generation):
~3k-4k words based upon the first two ground zero clusters

○ Content audit, consolidation, and URL structure


○ First draft

○ Client review

○ Second draft

○ Client review

○ Final

○ Content upgrade (offer)

○ Oversight of nurture sequence post-opt-in

● Key results

○ Keyword rankings

○ Traffic and sources

○ Lead volume

○ Lead scoring

○ Conversion rates

Months two and beyond focus on building out (1) a full strategy and editorial
calendar based on months 1-2 findings, (2) continuing to align content
creation and acquisition — primarily conversion rates from visitors and leads
to product entry — (3) additional pillar pages, and (4) guidance and editorial
oversight to make the process scalable in-house.

Monthly retainer: $10k


Finding Their Hell

Every piece of content you create has to do two things: (1) rescue its
audience from their own personal hell and (2) deliver them unto their own
personal heaven. Great content is about salvation … not sales.

First, your audience’s own hell:

1. What are the external forces of antagonism (enemies) that beset your
reader’s journey: people, things, and power structures?

● People

● Things

● Power structures

2. What are the internal forces of antagonism: character flaws (bad habits),
physical limitations, and mental blank spots?

● Character flaws

● Physical limitations

● Mental blank spots

3. What does your audience hate either about their life or job? What makes
them angry? What “triggers” outrage?


4. What additional problems do their hates create? How do they conspire

and accumulate?

5. What are the numerical consequences of their hates? Can you quantify
the total — and often uncounted — costs?

6. What are your audience’s nagging frustrations? Their headaches? What

do they wake up groaning and grumbling about?

7. What do they complain about to their friends, family, and colleagues?

How do these complaints differ in context?

8. What diseases (metaphorically) plague them? Where do they hurt? Are the
wounds fresh? Or are they scar tissue?

9. What are the symptoms of those diseases? Are they acute? Do they “flare-
up” under specific conditions? Are they chronic?

10. What does your audience go to bed dreading or stay up at night churning
over? What steals their sleep and haunts their dreams?

11. What is your audience embarrassed or insecure about? What are they
hiding? What do they hope “no one notices”?

12. What mysteries can’t they find an answer to? What confuses them?

13. If your audience had a magic wand — or a single-wish genuine — what’s

the first thing they would instantly banish?


14. What roadblocks have cut off their journey? What speed-bumps slow
them down?

15. Where have they failed before? Experienced rejection? Where have they
heard and keeping hearing: “No”?

Second, your audience’s hell as it relates to you …

16. What are the most awkward or inconvenient things about your type of

17. What does your audience distrust about your service or product? What
are they suspicious of or have a hard time swallowing?

18. What are the biggest barriers to becoming a customer? What are their

19. What trade-offs (i.e., benefits versus costs) aren’t they willing to make?

20. What’s the one, first-step that — if they took — would give them a foretaste of
heaven? What are the appetizers before the main meal?


iconiContent Portfolio: A
Shortlist of Long-Form
A lot of clients ask about design, so the parentheses note whether the linked
content’s visuals — or the Content Upgrades (PDFs) — were created by me or
the client’s in-house design team …

1. Shopify: What Is the Future of Ecommerce? 10 Insights on the Evolution

of an Industry (mixed Aaron + in-house design team)

2. Shopify: Global Ecommerce Statistics and Trends to Launch Your

Business Beyond Borders (mixed Aaron + in-house design team)

Content Upgrade: The Global Ecommerce Playbook: Map, Launch, and

Scale international (PDF) (in-house design team)

3. Shopify: Holiday Ecommerce: 10 Marketing Strategies from +$1.5B in

Online Sales (Aaron designed)

Content Upgrade: Holiday Ecommerce Revealed: Brands Generating Over

$10m/Year in Revenue Share Their Plans, Strategies, and Insights (PDF)
(in-house design team)

4. Common Thread Collective: Holiday Marketing E-commerce Strategy:

How to Set a Foundation of Profit & ‘Peace’ (Aaron design)

5. Planning Your Black Friday Social Media Campaigns: Not a Listicle, an

Ecommerce Calendar (That’s Useful) (Aaron design)

6. PostFunnel: The Complete A-Z Facebook Ads Guide (PDF) (in-house


7. TradeGecko: Inventory Management: Ultimate Guide to What, Why &

How (Pillar Page) (in-house design)

8. Groove: 15 Customer Service Skills & How to Improve Each One Step-by-
Step (in-house design)


9. Groove: What is Good Customer Service? A Definition, Data & 11 Qualities

of Exceptional Support (in-house design)

10. QuickBooks: How to start a business in 15 steps: Guide, checklist, and

canvas (Aaron designed)

11. QuickBooks: How to write a business plan (template): 10 steps, 5 tips, and
examples to guide you (Aaron designed)



The Ultimate Content

Creation Checklist
21 Strategic Questions to Supercharge
Your Focus Before You Hire a Marketer or
Pen a Single Word

A few preliminary notes …

The following questions, and especially your responses, are meant to prompt
initial, gut-level observations.


Naturally, the more information you provide — and the more concrete and
specific that information is — the better my understanding of your needs and
goals will be.

Just remember, this is only a first step. What we’re after are facts, feelings,
dreams, and initial data. We’ll do much more exploring later, so just relax,
write from the heart, and be as honest as possible.

Before we get to your content, I want to get to know you … the real you.

This might seem counterintuitive. After all, your business isn’t about “you.”
It’s about “them”: your prospects, audience, customers, and clients.

The problem is: most business owners are simply busy being busy.

It’s what Charles E. Hummel called the “tyranny of the urgent”: instead of
focusing on what really matters — the tasks and projects that truly move your
business’ needle and create lasting, long-term value — we get bogged down
by the virtually endless stream menial, trivial, daily demands.

Don’t worry; I won’t get too touchy-feely (after all, we just met). But … I am
going to get philosophical. Why? Because …

Aristotle was right: “The unexamined life is not worth living.” More
to the point: “The unexamined business is not worth running.”

The fundamental mistake owners, entrepreneurs, and managers make is

putting their business existence before their personal essence. What do I

Putting your business existence before your personal essence means

elevating what you do — your services and products — above who you are —
your passions and values.

This common mistake drains you of focus, purpose, and (in the end) genuine
excellence. Moreover, it robs you of not only professional success but
personal happiness as well.


Until you have a clear and compelling answer to the question, “What do I
really want?” you don’t stand a chance of convincing other people to follow
you. And, of course, “follow you” is a just a nice euphemism for “buy your

So, let’s start with …


1. What are you most passionate about? What do you love not just about
what you do (i.e., your business) but about who you are (i.e., your life)?

2. Who do you look to as the living embodiment this passion? What experts,
industry leaders, and other businesses do you most admire? Who have
you learned the most from? What books, seminars, websites, or training
programs fire you up?


3. What businesses (especially websites) are currently offering the services

you’re interested in offering as well?

Your Values

Start by listing your top five one-to-two-word defining or aspirational values

in the space provided.

Then, define them. Explain what each value mean to you in a one-to-two-line
definition. Last, apply them. Relate those values to real life: put some flesh on
‘em. Describe a personal example or illustration.

Value 1: ________________________




Value 2: ________________________



Value 3: ________________________




Value 4: ________________________



Value 5: ________________________



4. How do your passions and values apply to your business?

This might take the form of a mission statement or some existing brand
collateral. If it does, great. Pull out whatever documents you have and
start aligning.

If you don’t have any existing documents, even better. Simply take your
five top values and write one addition sentence for each explaining how
that value applies to your products, services, or (especially) your audience.







5. What is the one idea—what we might call the one concept, the one
commitment, or the one promise—your business, service, or product is
built around?


Create a feature-to-benefit spreadsheet that ties each feature of your business to a specific benefit.
Describe as vividly and concretely as possible the “you” your customers will become when they use your
product or service.

Feature Benefit


6. What are your audience’s buying “hot buttons”?

7. When it comes to purchasing a product or service like yours, what issues,

considerations, values, or outcomes are most important to your
customer? For example, is your audience concerned with price, quality
(i.e., results), status, efficacy (i.e., speed), etc.?

Value Proposition

8. What makes your business, product, or service unique?


9. What (as you see it) is your value proposition? That is, why would your
ideal customer buy from you rather than one of your competitors? What
sets you apart?

10. Desirable: Is your value proposition focused on one key benefit or “mass
desire” powerfully verbalized?

11. Unique: Is your value proposition clearly differentiated from the

competition in at least one specific way?

12. Audience-Centered: Is your value proposition addressed directly to one

target market?

13. Simple: Is your value proposition clear, concise, and memorable?


14. Quantified: Is your value proposition supported by at least one piece of

concrete data?

Value Proposition Templates

Use one of the two fill-in-the-blank templates to make a rough draft of your Value Proposition.

15. “The only way for [target market] to [feature/action], so you [benefit/

16. “We do [feature/action] for [target market], but the difference is [blank]
so that you [benefit/outcome].”


17. What are your current communication strategies? How do you market
your business, product, or service? How do your customers retrieve
information about you (i.e., channels/media)?

18. Do you have a motto or tagline for your business, product, or service? If
not, would you like to explore creating one?

19. Does your business have a brand strategy? Core values? Mission
statement? Or identity?

20. Who is (or are) your major competitor(s) and where do you rank in your

21. What are your company’s short-term (6 months) and long-term (2-5
years) goals?