SlideShare a Scribd company logo
Developer’s Guide 
to Running Sales 
Teams…
http://developingsales.com 
Jeff Szczepanski 
Chief Operating Officer
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!!
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!
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!
Add More Features!!? 
Best Way to Increase 
Sales???
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.
Good sales execution is what 
sits between your Product 
and a Great Business 
Product 
Sales 
Execution 
Great 
Business
Building Sales Orgs in 3 Phases 
Proving Product Value 
Understanding your Pitch 
Scaling the organization
Essence of Phase 1 
Proving a Market Exists for your 
Product and that people will pay 
money for it.
Phase 1 Goal 
Several paid customers who are 
getting value out of the product
Phase 1 -> Challenge 
Your Product 
Really, Really 
Stinks
Phase 1 -> Implication 
Customers are buying into your 
vision more than your product
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
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
Phase 2 
Proving Product Value 
Understanding your Pitch 
Scaling the organization
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
Goal of Phase 2 
Multiple Sales Reps 
Closing Deals on 
their Own
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
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”
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”
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!!
Phase 3 
Proving Product Value 
Understanding your Pitch 
Scaling the organization
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
Phase 3 Goal 
Jetting to your vacation home in Aspen, Colorado
Phase 3 Goal 
Predictable 
Revenue that 
is Scaling
Phase 3 Concepts 
Must Read Book!! 
(But ignore half of it)
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
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
Phase 3 Scaling Solution 
What if we put an experienced 
CTO/VP of Engineering 
in charge of Sales!!??
Developer's Guide to Running Sales Teams
WTF – Does that really help?
Phase 3 Insight 
Good Sales 
Management 
approaches parallel 
Good Software 
Development 
approaches!!
Properties of Successful Software 
Development
Smart and Gets Things Done 
Empowered Autonomous Individual Contributors
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
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
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
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.
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
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
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
Phase 3 Role Separation 
Team Leaders => Track Racing Pit Crew 
Sales Management => Garage Mechanics
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
Phase 3 Tools and Process
Phase 3 Tools and Process
Phase 3 Tools And Process
Phase 3 Tools and Process
Phase 3 Goal 
Predictable 
Revenue that 
is Scaling
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.
Thank you!!! 
talljeff@stackoverflow.com 
@inscitekjeff 
Blog: DevelopingSales.com

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Developer's Guide to Running Sales Teams

  • 1. Developer’s Guide to Running Sales Teams…
  • 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