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Enterprise Sales Basics
Ash Rust
ash@sterlingroad.com
Managing Partner, Sterling Road
Getting Feedback
Agenda
Customer Profiles
Closing Sales
Customer Success
1
2
3
4
Private and Confidential
What is an
Enterprise Sale
ü Product is sold to business
ü Contract is worth $10k+
USD/year
ü Less customers exist but more
money per customer
ü Harder to get their attention
but customers are loyal
Private and Confidential
Getting Feedback
1
Private and Confidential
Getting
Feedback
Best Channels
Network
introductions
Cold outreach –
Ask for advice
Conferences
Consulting
Private and Confidential
Getting
Feedback
Other Channels
Cold Outreach –
Sales emails/calls
Content Marketing
Ads
Private and Confidential
Hi Shona,
I’m Ash, the CEO of Acme. Based on your experience at AlphaNet and Beta.com, along with your
industry insights (I took a quick look at your conference talk), I thought you’d be a great addition to the
Acme Customer Advisory Board.
We’re building the board to get feedback on the Acme product from customers like you, and we want to
make sure it’s tailored to your specific needs. Members of the board will receive equity in the company
and help us build this much needed solution through their input.
If you’re interested, you can find more information on our website and the one-pager attached. The
board is almost complete, with 1 or 2 spots remaining, so please let me know if you’d like to schedule a
brief call.
I’m free at 11am PST Thursday and Friday this week, if either of those work for you?
Looking forward to chatting more!
Cold Outreach Template
Private and Confidential
Content Marketing Example
Private and Confidential
Customer Profiles
2
Customer
Profile
Allows you to target
your outreach
Makes lead
generation more
efficient
Private and Confidential
Create a
customer
profile
Business Size
e.g. 500-1,000 employees
Industry
e.g. manufacturing, defense, software
Location
e.g. Canada
Job Title
e.g. Director of Human Resources
Private and Confidential
Get Live!
Customer Profile < Getting Live
1st customer live can be anyone
Once live, test customer profiles
Private and Confidential
Make a list of potential titles of sales targets
Target end users first, then easier to convince
decision makers
Famous Logos?
Not worth prioritization
Who to Contact
Private and Confidential
ü Test profiles consecutively, not concurrently
ü Success/Failure states for each profile
ü Test demand from different profiles by asking
for upfront cash
Selling to Multiple Profiles
Private and Confidential
Closing Sales
3
Private and Confidential
Yes is not the same
as a paid invoice
Lots of obstacles to
overcome
Closing
Sales
Private and Confidential
Sales Process
Part 1
ü From Interview to Lead
ü Sell before Building
ü Objection Handling
ü Trial Periods
ü Pricing First Customers
Private and Confidential
From Interview to Lead
Ask for
advice
Ask for demo
feedback
Ask if demo solves
their problem
Ask for small
deployment
Private and Confidential
Do research and start with small talk
Customer Discovery Conversations
I see you live in
Austin, my sister
lives there. Does your wife
know Sarah
Smith at EY?
You dive? Have
you been to The
Great Barrier
Reef?
Have you been to
Handlebar Coffee
in the Village?
Private and Confidential
Then start asking more questions
Customer Discovery Conversations
What are your worst
problems in this area
(the problem your
solution fixes).
How much do
they cost you in
time/money?
How do you
currently solve
this? How much
does that cost?
What would make
you consider
switching to
another provider?
What is your
process for new
vendors? Need
approvals?
What legal/security/
compliance requirements
do they have for vendors?
What other
systems would we
need to integrate
with to deploy?
Private and Confidential
Sell Before Building
Use Demo Tools
Build Simple Apps
Expect to Sell
Services
Use Legacy
Integrations Compliance or security to help close
Private and Confidential
Objection
Handling
ü Build vs Buy
ü Missing Features
ü Cost and Risk
ü Track Q&A in a shared,
editable document
Private and Confidential
ü Paid trials are ideal but not always possible
ü Ok to offer 30-90 day trials. Shorter usually better.
ü Build customer reliance first, then talk about $$
Trial Periods
Private and Confidential
1st : Free
Doesn’t need to match
customer profile
2nd : $1
Matches customer profile
(same for all, from now on)
3rd : Fair Price
10x COGS or 10% of ROI
Pricing First Customers
4th : 3x Previous
3x 3rd customer’s final price
Expect to negotiate down
5th : 3x Previous
3x 4th customer’s final price
Expect to negotiate down
Beyond : Expect variance
E.g. lower charge for case study customer
Private and Confidential
Sales Process
Part 2
ü Business Models
ü Closing Tactics
ü Navigating Internal
Stakeholders
ü Metric & Funnel
Guidelines
Private and Confidential
Most Enterprise Tech Companies Sell their Product as a Service
Business Models
Free Trial Freemium Paid Pilot
Variable,
Usage Based
Open Source
Private and Confidential
Closing Tactics
ü Complete small task
ü Free service until
previous vendor
contract expires
ü Professional services
Private and Confidential
End user not always a decision maker
• Different stakeholders have different goals
• Treat everyone as well as your internal champion
Be prepared to provide certification or similar
Navigating Internal Stakeholders
Private and Confidential
10-30%
20-40%
Enterprise Funnel Metrics
Outreach response rates
Outreach to
“interested” leads
Interested to
signed
contract
10-30%
Private and Confidential
Sales Cycles by Annual Contract Size
2 – 4
weeks
$100k+ year
$10k - $50k year
$1k - $10k
$100 - $1k
4 -12
weeks
3 -12
months
1.5 - 9
months
Private and Confidential
Website visitor signup rate
SMB Conversion Expectations
1-3% 10-30%
10-30%
App download signup rate
Trial conversion rate
Under 3%
Logo churn month
Private and Confidential
Customer Success
4
Private and Confidential
‘YES’ is only half
of the battle
Ensure customer
success for the
long term
Customer
Success
Private and Confidential
ü First 10 Deployments
ü Regular User Interviews
ü Measuring Engagement
ü Onboarding Iteration
ü Upselling
Customer
Success
Private and Confidential
Handhold customers through each step
Kickoff meeting with stakeholders, onsite if possible
Regular stakeholder meetings
SWAG, thank you cards help
First 10 Deployments
Private and Confidential
Regular User Interviews
Ask for weekly
interviews
Does your
offering solve
their problem?
Why are they
(not) using it?
What do they
want to change?
Let them talk…
Private and Confidential
Measure Engagement
Track individual usage
Your database or event tracking (Metabase is free)
Pick an engagement metric
Make it a core metric for your company
Identify power users and lost users, learn from behavior
patterns
Private and Confidential
Track earliest usage of power users
Push new users to the actions that create
power users
Iterate. A lot.
Onboarding Iteration
Private and Confidential
Ask happy customers for internal and external referrals
Ask customers what else they need
Test demand – alpha trials, upfront payments
Upsell
Enterprise Sales Basics
Ash Rust
ash@sterlingroad.com
Managing Partner, Sterling Road

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Enterprise Sales Basics - Sterling Road

  • 1. Enterprise Sales Basics Ash Rust ash@sterlingroad.com Managing Partner, Sterling Road
  • 2. Getting Feedback Agenda Customer Profiles Closing Sales Customer Success 1 2 3 4
  • 3. Private and Confidential What is an Enterprise Sale ü Product is sold to business ü Contract is worth $10k+ USD/year ü Less customers exist but more money per customer ü Harder to get their attention but customers are loyal
  • 5. Private and Confidential Getting Feedback Best Channels Network introductions Cold outreach – Ask for advice Conferences Consulting
  • 6. Private and Confidential Getting Feedback Other Channels Cold Outreach – Sales emails/calls Content Marketing Ads
  • 7. Private and Confidential Hi Shona, I’m Ash, the CEO of Acme. Based on your experience at AlphaNet and Beta.com, along with your industry insights (I took a quick look at your conference talk), I thought you’d be a great addition to the Acme Customer Advisory Board. We’re building the board to get feedback on the Acme product from customers like you, and we want to make sure it’s tailored to your specific needs. Members of the board will receive equity in the company and help us build this much needed solution through their input. If you’re interested, you can find more information on our website and the one-pager attached. The board is almost complete, with 1 or 2 spots remaining, so please let me know if you’d like to schedule a brief call. I’m free at 11am PST Thursday and Friday this week, if either of those work for you? Looking forward to chatting more! Cold Outreach Template
  • 10. Customer Profile Allows you to target your outreach Makes lead generation more efficient
  • 11. Private and Confidential Create a customer profile Business Size e.g. 500-1,000 employees Industry e.g. manufacturing, defense, software Location e.g. Canada Job Title e.g. Director of Human Resources
  • 12. Private and Confidential Get Live! Customer Profile < Getting Live 1st customer live can be anyone Once live, test customer profiles
  • 13. Private and Confidential Make a list of potential titles of sales targets Target end users first, then easier to convince decision makers Famous Logos? Not worth prioritization Who to Contact
  • 14. Private and Confidential ü Test profiles consecutively, not concurrently ü Success/Failure states for each profile ü Test demand from different profiles by asking for upfront cash Selling to Multiple Profiles
  • 16. Private and Confidential Yes is not the same as a paid invoice Lots of obstacles to overcome Closing Sales
  • 17. Private and Confidential Sales Process Part 1 ü From Interview to Lead ü Sell before Building ü Objection Handling ü Trial Periods ü Pricing First Customers
  • 18. Private and Confidential From Interview to Lead Ask for advice Ask for demo feedback Ask if demo solves their problem Ask for small deployment
  • 19. Private and Confidential Do research and start with small talk Customer Discovery Conversations I see you live in Austin, my sister lives there. Does your wife know Sarah Smith at EY? You dive? Have you been to The Great Barrier Reef? Have you been to Handlebar Coffee in the Village?
  • 20. Private and Confidential Then start asking more questions Customer Discovery Conversations What are your worst problems in this area (the problem your solution fixes). How much do they cost you in time/money? How do you currently solve this? How much does that cost? What would make you consider switching to another provider? What is your process for new vendors? Need approvals? What legal/security/ compliance requirements do they have for vendors? What other systems would we need to integrate with to deploy?
  • 21. Private and Confidential Sell Before Building Use Demo Tools Build Simple Apps Expect to Sell Services Use Legacy Integrations Compliance or security to help close
  • 22. Private and Confidential Objection Handling ü Build vs Buy ü Missing Features ü Cost and Risk ü Track Q&A in a shared, editable document
  • 23. Private and Confidential ü Paid trials are ideal but not always possible ü Ok to offer 30-90 day trials. Shorter usually better. ü Build customer reliance first, then talk about $$ Trial Periods
  • 24. Private and Confidential 1st : Free Doesn’t need to match customer profile 2nd : $1 Matches customer profile (same for all, from now on) 3rd : Fair Price 10x COGS or 10% of ROI Pricing First Customers 4th : 3x Previous 3x 3rd customer’s final price Expect to negotiate down 5th : 3x Previous 3x 4th customer’s final price Expect to negotiate down Beyond : Expect variance E.g. lower charge for case study customer
  • 25. Private and Confidential Sales Process Part 2 ü Business Models ü Closing Tactics ü Navigating Internal Stakeholders ü Metric & Funnel Guidelines
  • 26. Private and Confidential Most Enterprise Tech Companies Sell their Product as a Service Business Models Free Trial Freemium Paid Pilot Variable, Usage Based Open Source
  • 27. Private and Confidential Closing Tactics ü Complete small task ü Free service until previous vendor contract expires ü Professional services
  • 28. Private and Confidential End user not always a decision maker • Different stakeholders have different goals • Treat everyone as well as your internal champion Be prepared to provide certification or similar Navigating Internal Stakeholders
  • 29. Private and Confidential 10-30% 20-40% Enterprise Funnel Metrics Outreach response rates Outreach to “interested” leads Interested to signed contract 10-30%
  • 30. Private and Confidential Sales Cycles by Annual Contract Size 2 – 4 weeks $100k+ year $10k - $50k year $1k - $10k $100 - $1k 4 -12 weeks 3 -12 months 1.5 - 9 months
  • 31. Private and Confidential Website visitor signup rate SMB Conversion Expectations 1-3% 10-30% 10-30% App download signup rate Trial conversion rate Under 3% Logo churn month
  • 33. Private and Confidential ‘YES’ is only half of the battle Ensure customer success for the long term Customer Success
  • 34. Private and Confidential ü First 10 Deployments ü Regular User Interviews ü Measuring Engagement ü Onboarding Iteration ü Upselling Customer Success
  • 35. Private and Confidential Handhold customers through each step Kickoff meeting with stakeholders, onsite if possible Regular stakeholder meetings SWAG, thank you cards help First 10 Deployments
  • 36. Private and Confidential Regular User Interviews Ask for weekly interviews Does your offering solve their problem? Why are they (not) using it? What do they want to change? Let them talk…
  • 37. Private and Confidential Measure Engagement Track individual usage Your database or event tracking (Metabase is free) Pick an engagement metric Make it a core metric for your company Identify power users and lost users, learn from behavior patterns
  • 38. Private and Confidential Track earliest usage of power users Push new users to the actions that create power users Iterate. A lot. Onboarding Iteration
  • 39. Private and Confidential Ask happy customers for internal and external referrals Ask customers what else they need Test demand – alpha trials, upfront payments Upsell
  • 40. Enterprise Sales Basics Ash Rust ash@sterlingroad.com Managing Partner, Sterling Road