I delivered this talk to the Communitech Senior Sales Peer 2 Peer group, where we discussed some of the toughest sales a CEO will ever go through. I share some personal anecdotes and tactics that worked well for me.

1. Your CEO’s Most Stressful
Sales
Joseph Fung, CEO @ Kiite
Senior Sales P2P
20 Feb 2018

2. I love imagining,
building and selling
software.
2

3. Sales are a measure of how well
you solve a problem and how
large that problem is
3
Why do I love selling?

4. First Sales of a New Product
4

5. 5
New Market
New Pain
New Tech
New Pricing
What could go wrong?
We were moving from selling services
to selling a product.

6. If you could have this solution
today, how much would you pay?
6
We invited 10 prospects in, demoed, and asked them
Then we gave them that price.

7. Raising Equity Investments
7

8. US $1M < 3 Months
8
“Keeping in mind I hold you in
extremely high regard, I thought you
were completely crazy. I never
believed for a moment that you’d
actually pull it off.”
We had ambitious fundraising goals

9. ● Surround Them with Social
Proof
Make sure they hear about you from more than just you
● Responsiveness Wins
<5 Min phone response time to emails and messages
● Set the Pace Whenever Possible
Follow up faster, and with better results, than you promissed 9

10. First Sales Through a Channel
10

11. 11
We started off with a completely balanced relationship...
$300K ARR
16 Employees
$5,000 ACV
> $350M ARR
~ 2,500 Employees
~ $60,000 ACV

12. 12
And showed up strong at their user conference

13. 13
3-Pronged Strategy
1. Make Reps look good
2. Make Customer feel smart
3. Nail The Price
● Dedicated Account Reps
● Blazing Fast Response
● Tablet Demo Unit
● 411 Roadshows
● Tailored Demos
● Integration Info Sheets
● Competitive Battle Cards
● Joint Customer Case Studies
● Tech Checks
● Coffee Profiles

14. Partner reps closed bigger deals
faster when we were in the mix
14
By focusing on making the partner rep look good, we could help ensure their deal. If our product was
considered as part of the deal, then it was only a matter of time till they’d complete our purchase too.
Corollary: there’s no point in pitching our product if they are going to lose their deal

15. Selling the Company
15

16. 16
Sell 26%+
Grow Sales & Marketing
Risks in Sales Model
Increasing US Focus
Product Gap
Sell 100%
600+ Sales Reps
Proven Model
Grow Locally
Compliance Gaps
vs.
vs.
vs.
vs.
vs.
VC vs. VC vs.
NetSuite

17. Of Acquisitions Fail
At least according to many pundits and bloggers. This stat is often-quoted and never proven. I’d love to
quote a more reputable source but couldn’t find one.
17
90%

18. What worked for us
1. Find a Champion and an Insider
2. Watch for professional “Transaction Closers”
3. Don’t stop selling, even after the close
4. Focus on total value, not pricing structure
18

19. 19
4 years later we showed up strong at their user conference.
Again.

20. 20
Intelligent Sales
Assistants

21. First Sales Through an AI
21

22. 22

23. “AI will redefine not just the role of the salesperson but also
that of sales management. Managers will have access to a
whole new set of metrics on not just the members of their
teams but on buyers as well. AI will enable them to coach and
mentor people in a far more individualized way than ever
before, and we need to ensure that managers have the
knowledge and skills necessary to make use of that power.”
Jim Dickie, CSO Insights
23

24. 24
83%
of millennials in the workplace
trust advice from intelligent
machines .
Accenture
75%
of the workplace will be made
up of millennials by 2025.
Forbes

25. … the building blocks all exist
25

26. By gathering the insights from every
opportunity, managers can understand
what it takes to win a deal and identify
anything at-risk before it’s too late.
26
Behavioral
Analytics

27. Voice Analytics Stop digging through hours of customer
calls for hidden gems of insight. TalkIQ
proactively surfaces the most important
trends in customer sentiment from all of
your customer conversations.
27

28. Document
Synthesis
Email messages crafted in response to a
lead’s initial inquiry sound like they are
coming from a live person. The persona
uses a friendly, colloquial conversational
style..
28

29. Chat Assistants
Real time answers to tough questions help
your reps ramp up, move more quickly, and
close more deals. Predictive intelligence
shares insights before they even think to
ask.
29

30. AI-Assisted Sales Reps?
30
● Each rep will manage more deals simultaneously
● More time reviewing, less time writing
● Less opportunity to train as a BDR

31. Will AI transform every rep into
a team lead?
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32. 32
✉ joseph@kiite.ai
@josephfung
✆ 519-616-1377