The document discusses a company's transition from targeting small-to-medium businesses to focusing on mid-market and enterprise customers. It describes how the company identified its target customers as large independent brokerages and luxury franchise groups. It then details how the company built customer personas, developed prospect lists through research and by attending conferences, and created an outbound sales engine of emails and calls. This transition helped the company grow its annual recurring revenue from $1 million to $4.3 million over two years and increase its enterprise customer base from 18 to 115. Lessons learned included iterating sales processes, balancing lead generation and quality, providing more sales training, and pursuing larger customers sooner.

1. Movin’ on up!
How we transitioned from SMB to mid-market/enterprise
March 2019

2. Movin’ on up!
How we transitioned from SMB to mid-market/enterprise
March 2019

3. Jan 2017
17%
Dec 2018
43%

6. What we’ll cover today
● Why we decided to shift upmarket
● The Big Hows
○ How we identified our target customer
○ How we built our prospect list
○ How we built the outreach engine to reach
prospects
○ How we leveraged initial success to breed more
success
● If we did it all over again…

9. We had some success with INBOUND big customers
May 2014
$200k ARR
March 2015
$125k ARR

11. We had to be honest with ourselves:
who was our target customer?

14. We ultimately got to a clear assessment on
pros/cons for each segment of our market

15. We ultimately focused on two major groups
Large independents Luxury franchises

16. With focus, building out the sales
engine was straightforward…
albeit time-consuming.

20. We built personas for each executive buyer
● Managing broker / owner
● COO
● Head of Sales
● Head of Marketing
● Head of Training
● Head of IT

21. High quality lead research for $5/hr

24. Over time, we become more
sophisticated with list building

25. Example #1: going to a conference
ZIP code radius search

26. Example #2: getting targeted with competitors

29. We built out an outbound engine
● Mix of generic and
personalized emails, as well
as calls → typically over 2-3
weeks
● Went for volume = 20 new
contacts/day (at scale that
was ~150 touches/day)

33. Jan 2017 Dec 2018
$1.0M ARR
$4.3M ARR
In two years…
18 → 115 enterprise customers
17% to 43% of total ARR

34. 17% of all Sotheby’s brokerages
became our customers

35. By end of last year, 8 of the
largest 20 US brokerages were
our customers

36. There’s a big herd
mentality when
selling to the
enterprise
We sought to feature
our top customers
everywhere

39. Biggest lesson learned:
iterate, iterate, iterate

40. #1: Different business models lead to wildly
different results
Usage-based User bill-back Flat fee

41. #2: Once you build the engine, you need to keep
it fed
Had to balance
keeping the sales
team fed with leads
& keeping lead
quality high

42. #3: We should have done way more sales training

43. #4: We should have done this so much sooner!

44. Reach out with any questions!
Tony Cappaert
tony@nakedstartup.com
617-680-2764