- The document discusses how startups can retool their business to target larger enterprise customers by focusing on three key areas: (1) repositioning to change market perception, (2) reengineering go-to-market strategies to match buyer considerations, and (3) retooling internal systems and processes to prioritize speed, data-driven decisions, and cross-functional alignment. - It provides examples of positioning problems enterprises may have and strategies like clarifying value propositions, updated messaging, and internal documentation. - Advice on reengineering sales motions includes tailoring approaches based on buyer types and consideration levels, as well as optimizing channels, tripwires, and balancing short and long-

1. Breaking into the Enterprise: How to retool your
startup to move up market
Hana Abaza
@hanaabaza

2. There’s no such thing as a
marketing problem.

3. There’s no such thing as a
marketing problem.
There are only business problems.

4. But first… story time :)

5. Shopify Revenue
0
175
350
525
700
2012 2013 2014 2015 2016 2017

6. Shopify Revenue
0
1250
2500
3750
5000
2012 2013 2014 2015 2016 2017 2018 2019 2020 2021

7. • Super shitty
• Super expensive
• People buy it anyway
The Whitespace Trifecta

12. • Market perception
• Internal systems
• Internal perception
Here’s why…

13. • (re) Positioning
• Reengineer your GTM
• Retool internally
Three things

14. (re) Positioning

15. - April Dunford, Ambient Strategy
“Marketing is about making it easy to
fi
nd, evaluate and
buy your product. Positioning is
fi
guring out what your
product is in the
fi
rst place.”

16. - April Dunford, Ambient Strategy
“Marketing can polish a turd. Positioning can
turn turds into fertilizer.”

17. What positioning problem are you solving for?

18. Problem #1
How do we change market
perception?

20. Small Merchants Large Merchants
Market Large and Broad Small and Niche
Competitive
alternatives
DIY (e.g. social)
SaaS platforms
Website builders
Bespoke solutions
MM/Enterprise software
Shopify Advanced
Pricing
14-Day Free Trial
$9-$300/mth
No Free Trial
12-Month Contract
$2,000/mth
Product All in one, simplicity
Part of a system, more capabilities,
security, integrations, customization etc.
Context

21. “The worst career move I could make
is choosing Shopify and being wrong.”
- Director of Ecommerce (DTC brand)

22. - CMO (Multinational CPG)
“How could something that works for a
10-person company be the same product
you’re selling to me, a 10,000-person
company?”

23. - VP of Technology (Traditional Retailer)
“If you lined up a bunch of CIOs they’d
all say that Salesforce, SAP, Oracle
and those kinds of vendors are the
safer bets.”

24. • Establishing shared values helps overcome objections and manage tradeoffs
• Flexibility vs. feature comparisons
• SaaS vs. on premise
• Distributed commerce
• New customers vs. upgrades
• Competitive alternatives were more complex (very broad, Shopify vs. Shopify)
Insights

25. • Shared language and understanding of your worldview
• Competitive alternatives (and how to position against them)
• Clear, crisp and concise internal documentation
• Internal comms plan / enablement
• Reframing product value props
• Updated messaging and language (all surfaces/assets)
Outcomes

26. Problem #2
WTF are you anyway?

27. We’re a lightweight CMS for content marketers.
How it started…

28. We’re a shitty version of Wordpress that part
of your marketing team might use.
What buyers heard…

29. Problem #3
Why should I pick you?

31. 1. Thousands of signals.
2. Who you interact with.
3. Traditional engagements (likes, shares).
4. Interests.
1. What you watch.
2. How much of it you watch.
3. Engagement with sound.
4. Likes and shares.
1. What you watch.
2. How much of it you watch.
3. When you watch.
4. Categories and genres.
Social Entertainment

32. 2015–2019 2019–2021 2022–present

33. • Increase in pipeline (marketing + sales)
• Qualitative feedback from partners and customers
• Adoption of proprietary “engagement score” for use as a key KPI
Signals it’s working

34. Problem #4
There’s a global pandemic…
now what?

35. • Delete all plans
• Speed to launch became a key value prop
• Aspirational framing > Survival mode
Rapid repositioning

36. But how?

37. • DO buy April’s book
• DO get clear on the problem
• DON’T throw it at the marketing team
Dos & Don’ts

45. Reengineer your GTM

46. The best product doesn’t
always win.

47. The best product doesn’t
always win.
The product everyone uses wins.

49. There must be a mindset shift. What you are
optimizing for changes.

50. SMB Mid Market Enterprise
Target Market Large and Broad More focused, relatively broad Small and niche
Buyer Entrepreneur/Owner
C-suite/manager,
small buying group
Buying group, many
stakeholders/approvers
Sales Funnel Shorter, Few Steps Depends Longer, Many Steps
Drivers Marketing/Growth
Marketing, Partners,
Outbound/Outreach
Mix of inbound and outbound,
BD, strategic partners
GTM Motion
Self-serve and/or Human
Assisted
Human Centric, Human
Assisted, Self-Serve
Human centric
Characteristics

51. Cheap Expensive
Price
Many customers Few Customers
Market Size
Simple Complex
Complexity
High Low
Fit
B2C B2B
Customer
Single transaction Long lifetime
Relationship
Low High
Touch
Marketing & sales intersection
Degree
of
involvement
Degree of purchase consideration
0 100
100
Sales
Marketing

52. Different segments may need a different
buying process.

53. Degree
of
involvement
Degree of purchase consideration
0 100
100
Moving the intersection
Sales assist to self-serve moved the intersection
● Expand Upgrade pool
● Increased efficiency
● Higher velocity / lower CAC
● Reduce operational load
Sales
Marketing

54. • What’s your starting point?
• What is the degree of purchase consideration?
• What signals do you see in the buying process?
Factors to consider

55. • Identify growth levers
• Where and how you execute (channels/surfaces)
• Making the right tradeoffs
• Establishing the right tripwires
• Balancing short term and long term
Reaching buyers

56. • Certi
fi
ed partners program
• Shifted channel mix (divested and invested)
• Ramped up database marketing
• Throttled back volume from core Shopify to reduce noise
• Heavy sales training and enablement
• Layered in cross-sell motion
Where we invested

57. Retooling

58. Systems and processes that enable speed,
the telemetry to know what’s working, the
ability to make great decisions.

59. • Systems and tech stack
• Faster marketing execution
• Improved speed to lead
• Process and operations
• Deal approvals
• Budget approvals
Speed

60. As you scale, you get slower slowly. Then
bam💥. It becomes a major problem overnight.

61. • Data silos
• Flying blind = poor decisions
• De
fi
ne what matters
Telemetry

62. • Mindset shift —> clarity on what you’re optimizing for
• Interdependencies between teams
• XFN working model
Teams

63. PLG vs. B2B Acquisition
Converting customers that are already
in your product.
Selling customers on abstract idea, don’t
experience full value of the product.
Session
Lead
Prospect
Active Customer
Awareness Awareness
Touchpoints
Lead
Launch
Qualified
Sales cycle
Active Customer
Expansion
In Product
In Product
In Conversation

64. Interdependencies between teams
Sales Toolkit
● Pitch decks
● Case studies
● Testimonials
● Competitive talk tracks
● Market insights
MARKETING SALES
BUYERS: DECISION MAKERS,
STAKEHOLDERS, INFLUENCERS
BUYERS: DECISION MAKERS,
STAKEHOLDERS, INFLUENCERS
SALES ENABLEMENT
Feedback loop

65. Interdependencies between teams
Sales Toolkit
● Pitch decks
● Case studies
● Testimonials
● Competitive talk tracks
● Market insights
MARKETING SALES
BUYERS: DECISION MAKERS,
STAKEHOLDERS, INFLUENCERS
BUYERS: DECISION MAKERS,
STAKEHOLDERS, INFLUENCERS
SALES ENABLEMENT
Feedback loop
Product
Feedback

67. Rapid alignment helps you make great
decisions faster, consensus slows you down.

68. Let’s recap

69. Get clear on your positioning problem and
desired outcomes.

70. Engineer a GTM that matches your buyers
consideration level and the context around
your product.

71. Retool internally enable speed, invest in the
telemetry to measure what works, and give people
the ability to make great decisions.