This document outlines best practices for building and scaling a sales organization across three phases: 1) Proving product value with founders selling the vision, 2) Understanding the sales pitch with multiple reps closing deals, and 3) Scaling to predictable revenue growth. Key recommendations include empowering autonomous reps, developing sales skills like engineering skills, using agile processes, and separating performance metrics from compensation to reward people rather than manage them. The overall message is that good sales management parallels good software development approaches.

1. Developer’s Guide
to Running Sales
Teams…

2. http://developingsales.com
Jeff Szczepanski
Chief Operating Officer

3. Common Startup Plan
1.Idea!
2.Technical Co-Founders
3.Raise Money
4.Build Great Product
5.Hire VP of Sales
ie: ‘Needz Sales’
6.Profit!!

4. Common Startup Outcome
1.Idea!
2.Technical Co-Founders
3.Raise Money
4.Build Product
5.While( Cash Remains )
Hire VP of Sales
<some stuff happens>
Wait 12 to 18 months
Fire VP of Sales
6. FAIL!

5. Common Startup Outcome
1.Idea!
2.Technical Co-Founders
3.Raise Money
4.Build Product
5.While( Cash Remains )
Hire VP of Sales
<stuff happens>
Wait 12 to 18 months
Fire VP of Sales
6. FAIL!

6. Add More Features!!?
Best Way to Increase
Sales???

7. Add More Features!!?
Best Way to Increase
Sales???
No, it’s cheating because it
expands your addressable
market, it doesn’t increase
actual rate of penetration.

8. Good sales execution is what
sits between your Product
and a Great Business
Product
Sales
Execution
Great
Business

9. Building Sales Orgs in 3 Phases
Proving Product Value
Understanding your Pitch
Scaling the organization

10. Essence of Phase 1
Proving a Market Exists for your
Product and that people will pay
money for it.

11. Phase 1 Goal
Several paid customers who are
getting value out of the product

12. Phase 1 -> Challenge
Your Product
Really, Really
Stinks

13. Phase 1 -> Implication
Customers are buying into your
vision more than your product

14. Phase 1 -> Activities
• Product is rapidly evolving
• Founders need to be out there
selling and proving the vision
Key Point: Professional Sales People Not
Needed (nor desired) in this phase

15. Phase 1 Best Practices
• Lean Startup Concepts
– Getting to Minimum Viable Product
• Founder selling of the vision
• Tight Feedback Loops without Filters
• Talk to BUYERS, not just Users
– all the personas in the value chain
• No Free Stuff: Prove Value
• Test your Pricing

16. Phase 2
Proving Product Value
Understanding your Pitch
Scaling the organization

17. Phase 2 Entry Foundations
• A product that is proving useful
– Doesn’t completely suck anymore
– Graduating from beta phases
• Multiple Paying Customers
– People Have paid real money
• Lists of Possible Future Customers
• Good sense of a Workable Price Point

18. Goal of Phase 2
Multiple Sales Reps
Closing Deals on
their Own

19. Phase 2: Sales Rep Hiring Profile
• Not their first Sales Job
– Proven ability to sell something
– At least modestly consciously competent
– Smart, Hungary, buy into your vision
– Genuinely like solving problems
• BUT Avoid Very Experienced Reps
– Expect to make tons of money immediately
– Expect too much from the product
– Preconceived notions on how to sell product

20. Common Phase 2 Problem
FOUNDER: “I can close customers
myself without any problem, but
the reps I’ve hired can’t close the
deals on their own”

21. Common Phase 2 Problem
SALES REP: “I can’t close customer X
without feature Y”
and
SALES REP: “If I had Feature A, then I
could sell way more”

22. Phase 2 Best Practices
• You product will always suck to some extent
– Admit it to yourself, Admit it to the Sales Reps
– Sell what you have
• Get to at least 3 Sales Reps as fast as possible
– You want multiple petri dishes
• Aggressive Compensation Plan
– Want successful reps making a ton of money
• Fight all urges to use discounts to close deals
• Sales Manager not Needed yet
– But a good idea to be looking!!

23. Phase 3
Proving Product Value
Understanding your Pitch
Scaling the organization

24. Phase 3 Entry Foundations
• Multiple Self Sufficient Reps Closing Deals
• Happy Reps Making good money
• Lots of Positive Testimonials
– Product doesn’t totally stink anymore
• Lots of Paying Customers
– Repeat business
• Lots of Identifiable Prospects to Attack

25. Phase 3 Goal
Jetting to your vacation home in Aspen, Colorado

26. Phase 3 Goal
Predictable
Revenue that
is Scaling

27. Phase 3 Concepts
Must Read Book!!
(But ignore half of it)

28. Phase 3 Bad News
• Nature of Sales is Changing Rapidly
• Classic Management Methods Failing
• Experience != Expertise
• Poor at Predictions of Outcomes
• Seemingly More Art than Science
• No Magical Processes to Follow

29. Phase 3 Bad News
• Nature of Sales is Changing Rapidly
• Classic Management Methods Failing
• Experience != Expertise
• Poor at Predictions of Outcomes
• Seemingly More Art than Science
• No Magical Processes to Follow

30. Phase 3 Scaling Solution
What if we put an experienced
CTO/VP of Engineering
in charge of Sales!!??

32. WTF – Does that really help?

33. Phase 3 Insight
Good Sales
Management
approaches parallel
Good Software
Development
approaches!!

34. Properties of Successful Software
Development

35. Smart and Gets Things Done
Empowered Autonomous Individual Contributors

36. Understand Performance != Results
Software Development
• Discovering, Developing and
Finalizing Requirements
• System Architecture, Design
and Code Construction
• Quality Control including
effective testing and validation
• Task Estimation and Project
Management
• Deployment and Ongoing
Maintenance
A bunch of Separable
Skills that individuals
and the team must be
process capable of

37. Phase 3: Skills Development
Software Development
• Discovering, Developing and
Finalizing Requirements
• System Architecture, Design
and Code Construction
• Quality Control including
effective testing and validation
• Task Estimation and Project
Management
• Deployment and Ongoing
Maintenance
• Team Morale and Cadence
Sales Development
• Prospecting
• Questioning
• Proposal Development and
Pitching
• Objection Handling
• Closing Skills
• Negotiation
• Time and Pipeline
Management
• Team Morale and Cadence

38. Team Morale and Cadence
• Bottom Up Schedule Estimates
• Strive for Continuous and Steady Output
– Team Goals but No death marches
• Using Peer and Social Pressure vs. Edicts
– Setting Cultural Norms and Expectations
• Compensation Fairness
• Merit not tenure based Advancement

39. Phase 3 Sales Rep Role
Same as Phase 2 Rep!!
….but you can loosen up
the constraints a little
…this is just like on your
dev team as it grows.

40. Phase 3 Sales Rep
Each Rep runs their Own Small Business:
• End to End ownership of the relationships
• Sets their Own Forecasts
• Picks their Own Accounts
• No scripts, No quotas
• Works under shared best practices
• Supported by Team Leader and Sales Manager

41. Phase 3 Sales Manager
• This is the Line Manager of the Sales Reps
– Parallel to the Engineering Manager
• Primary Responsibility is Skills Development
• Removes Operational Barriers
– Helps define and build common infrastructure
• Works with a Longer Term Horizon
– More Quarter to Quarter than Day to Day
• Tends to Specialize as you Grow
– Splits into Operational Aspects and Skills Development
Aspects

42. Phase 3 Team Lead
• Drives Cadence and Morale of the Team
• Parallel to the Technical Team Dev Leads
• Walking Personification of Ideal Sales Rep
• Natural Leaders that enjoy Mentoring
• Player and a Coach -> Carries full account load
• Eyes and Ears for Sales Management
– Spot treatments not skills development

43. Phase 3 Role Separation
Team Leaders => Track Racing Pit Crew
Sales Management => Garage Mechanics

44. Phase 3 Tools and Process
SCRUM Sprint Based Process
• Team Based & driven by the Team Leads
• Operated as Joint Retrospective and Standup
• Breaks Monthly or Quarter Forecasting Cycles
into Week Long Sprints
• Reinforces Team Work and Shared Best Practices
• Friendly competition between Teams and Offices

45. Phase 3 Tools and Process

46. Phase 3 Tools and Process

47. Phase 3 Tools And Process

48. Phase 3 Tools and Process

49. Phase 3 Goal
Predictable
Revenue that
is Scaling

50. Phase 3 Best Practices
• First Phase with Professional Sales Manager(s)
• Separate Performance from Results
• Developing Suites of Skills in Each Rep
• Empower the Reps and Teams to Self Manage
• Each rep is running their own little business
• Real Time information: No Static Reporting
• PS: All Current CRM Systems Suck!!!
• Autonomy and empowerment is the name of the game
REMEMBER: Compensation System is a way to Reward
people. It is NOT a Management Tool.

51. Thank you!!!
talljeff@stackoverflow.com
@inscitekjeff
Blog: DevelopingSales.com