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Matt Blumberg. Startup CXO
Table of Contents
List of Tables
List of Illustrations
Guide
Pages
STARTUP CXO. A Field Guide to Scaling Up Your Company's Critical Functions and Teams
Foreword
Part One Introduction
Introduction
Chapter 1 The Nature of a CXO's Role
Chapter 2 Scaling a CXO
Part Two Finance and Administration
Chief Financial Officer
Chapter 3 In the Beginning: Laying the CFO Foundation
Chapter 4 Fundraising
Preparing for a Fundraising Event
The Pitch Deck
Chapter 5 Size of Opportunity
Chapter 6 Financial Plan
Chapter 7 Unit Economics and KPIs
Chapter 8 Investor Ecosystem Research
Chapter 9 Pricing and Valuation
Chapter 10 Due Diligence and Corporate Documentation
Chapter 11 Using External Counsel
Chapter 12 Operational Accounting
Accounting Rules Implementation
Chapter 13 Treasury and Cash Management
Chapter 14 Building an In‐House Accounting Team
Chapter 15 International Operations
Chapter 16 Strategic Finance
Sales
Service
Marketing
Legal
Good CFO/Bad CFO. Rob Krolik, Venture Capitalist and former CFO. Jeff Epstein, co-CEO, CFO, Apex Technology
Chapter 17 Other Areas to Partner With
Chapter 18 High Impact Areas for the Startup CFO as Partner
Interest to Order: Order to Cash
Chapter 19 Board and Shareholder Management
Chapter 20 Equity. Equity Management
Secondary/Tender Transactions
409a Valuations
Chapter 21 Mergers and Acquisitions (M&A) Buy‐Side
The Merger Model
Sell‐Side
Chapter 22 Bonus Section: What We Used for Our Internal Systems When We Started Bolster
Selected Systems. Communication: Slack
Project Management: Trello
Email and Calendar: Exchange
File Storage/Management: Google Drive Enterprise
Video Communication: Zoom
Web Analytics: Databox
System Password Management: 1Password
Product Storyboarding: StoriesOnBoard
Financial System: QuickBooks
Accounts Payable: Bill.com
Expense Management: Expensify
Equity Management: Carta
CRM: HubSpot
HRIS: Gusto
Calendar Management: Calendly
Payroll: Gusto
401k Provider: Guideline
Insurance Provider: Vouch
Key Processes Established
Chapter 23 CEO‐to‐CEO Advice About the Finance Role
Signs It's Time to Hire Your First CFO
When a Fractional CFO Might Be Enough
What Does Great Look Like in a CFO?
Signs Your CFO Isn't Scaling
How I Engage with the CFO
Part Three People and Human Resources
Chief People Officer
Chapter 24 Values and Culture
What I Look for in a Chief People Officer. Scott Dorsey. Managing Partner, High Alpha
Chapter 25 Diversity, Equity, and Inclusion (DE&I)
Chapter 26 Building Your Team
Chapter 27 Organizational Design and Operating Systems
Chapter 28 Team Development
Chapter 29 Leadership Development
Chapter 30 Talent and Performance Management
Chapter 31 Career Pathing
Chapter 32 Role‐Specific Learning and Development
Chapter 33 Employee Engagement
Chapter 34 Rewards and Recognition
Chapter 35 Reductions in Force
Chapter 36 Recruiting
Like an Organ Transplant. Matt Blumberg, CEO, Bolster
Chapter 37 Onboarding
Onboarding vs. Waterboarding. Matt Blumberg, CEO, Bolster
Chapter 38 Compensation
On Decision Making
Chapter 39 People Operations
Open Vacation
Open Vacation: Was It Worth It? Matt Blumberg, CEO, Bolster
Sabbatical Program
Sabbatical: Was It Worth It? Matt Blumberg, CEO, Bolster
As the employee
As the manager
Extended Parental Leave
Well‐being Day
Payroll and Insurance Benefits
Processes
Employee Documents
Office Management
Chapter 40 Systems
Conclusion
Chapter 41 CEO‐to‐CEO Advice About the People/HR Role
Signs It's Time to Hire Your First Chief People Officer
When a Fractional Chief People Officer Might Be Enough
What Does Great Look Like in a Chief People Officer?
Signs Your Chief People Officer Isn't Scaling
How I Engage with the Chief People Officer
Part Four Marketing
Chief Marketing Officer. What Is Marketing, Really?
Why Are French Fries Like Marketing? Matt Blumberg, CEO, Bolster
Chapter 42 Where to Start
Building and Maintaining a Brand
Chapter 43 Generating Demand for Sales
Market Research
Competitive Intelligence
Technology
Metric Definition
Chapter 44 Supporting the Company Culture
Recruitment Marketing
Internal Communications
Employee Engagement
Chapter 45 Breaking Down Marketing's Functions
Brand
Digital
Website
Email
Social
Advertising
Omni‐Channel
The Case for Grouping Brand and Digital Together
Chapter 46 Events
Types of Events
Event Planning
Partnering with Sales
Pre‐Event
Event Execution
Post‐Event
Using Data
Chapter 47 Content and Communications
Public Relations
Content Creation
Gated Versus Ungated?
Chapter 48 Product Marketing
Deliver
Create
Analyst Relations
Enable
Chapter 49 Marketing Operations
Technology
Process
Measurement
Strategic Planning
When to Start Marketing Operations
Chapter 50 Sales Development
Sales or Marketing?
Leadership
Where to Start
A Note on Working with Agencies
Chapter 51 Marketing as a Partner/Collaborating with the Rest of the C‐suite
What I Look for in a Chief Marketing Officer. Brad Feld. Foundry Group partner, Techstars co‐founder
Chapter 52 Building a Marketing Machine (Scaleup)
Growing Your Team
Execute Across Channels
Broaden Your Reach
Final Thoughts
Chapter 53 CEO‐to‐CEO Advice About the Marketing Role
Signs It's Time to Hire Your First CMO
When a Fractional CMO Might Be Enough
What Does Great Look Like in a CMO?
Signs Your CMO Isn't Scaling
How I Engage with the CMO
Part Five Sales
Chief Revenue Officer
Chapter 54 In the Beginning: From Prospect to Customer
Chapter 55 Hiring the Right People
Hire with Head or Heart?
Chapter 56 Profile of Successful Salespeople
Chapter 57 Some Myth Busting
Chapter 58 Compensating Sales Team Members
Incentive Compensation Revisited. Evolving Your Compensation Plans
Chapter 59 Pipeline
Chapter 60 Scaling the Sales Organization
Don't Blindly Promote Your Best Salesperson
Chapter 61 Scaling Your Team Through Culture
Avoid Special Treatment
Lone Wolf or Team Player
Chapter 62 Scaling Sales Process and Methodology
Chapter 63 Scaling the Operating System
Chapter 64 Marketing Alignment
What I Look for in a Startup Chief Revenue Officer/Head of Sales. Greg Sands, Founder, Managing Director at Costanoa Ventures
Chapter 65 Market Assessment and Alignment
Chapter 66 Expanding Distribution Channels
Chapter 67 Geographic Expansion
Chapter 68 Pricing and Packaging. Pricing
Packaging
Final Thoughts
The Wisdom of Anita. Matt Blumberg
Chapter 69 CEO‐to‐CEO Advice About the Sales Role
Signs It's Time to Hire Your First CRO
When a Fractional CRO Might Be Enough
What Does Great Look Like in a CRO?
Signs Your CRO Isn't Scaling
How I Engage with the CRO
Part Six Business/Corporate Development
Chief Business Development Officer. To Create a CBDO or Not?
The CBDO Is an Ambassador
Chapter 70 How to Make the Biggest Impact as a CBDO
Chapter 71 Building Your Influence Internally
Chapter 72 Building Your Influence Externally
What I Look for in a Startup Business Development and Partnerships Leader. Greg Sands, Founder, Managing Director at Costanoa Ventures
Chapter 73 Where Internal and External Meet: Your Relationship with Your CEO
Chapter 74 Influence Meets Operating System
Chapter 75 Develop External Trust for the Company
Chapter 76 Build Your Influence in Strategy
Chapter 77 Building Your Influence in Business Development. Outbound
Inbound
Chapter 78 When Things Go Wrong in a Partnership…and They Will
Chapter 79 Geographic Expansion
Chapter 80 M&A: Buy Side
Chapter 81 M&A: Sell Side
Final Thoughts
Chapter 82 CEO‐to‐CEO Advice About the Business/Corporate Development Role
Signs It's Time to Hire Your First CBDO
When a Fractional CBDO Might Be Enough
What Does Great Look Like in a CBDO?
Signs Your CBDO Isn't Scaling
How I Engage with the CBDO
Part Seven Customer Success/Account Management
Chief Customer Officer. Welcome to the New World
Chapter 83 Five Misperceptions
Chapter 84 Startup Customer Success Organization
What I Look for in a Chief Customer Officer. Guy Turner, Managing Partner Hyde Park Venture Partners
Chapter 85 Scaling the Service Organization
Chapter 86 Timing: When to Hire Your Team
Chapter 87 Customer Segmentation and Journey
Segment Your Customers
Set an Appropriate Customer Experience for Each Segment
Coordinate with Sales
Chapter 88 Understanding Customers
Chapter 89 Understanding Customers Through Metrics
Onboarding Phase Metrics
Activation Phase Metrics
Use Phase Metrics
Renewal
Chapter 90 Foundations of a Great Customer Service Organization
Data
Technology
People
Chapter 91 Building an Effective Team
Chapter 92 Partnering with the Organization
Chapter 93 Five Eternal Questions
1 How Should I Structure Variable Compensation for the Customer Success Team?
2 Who Does the Upsell?
3 Doesn't the Customer Service Organization Own Churn?
4 Shouldn't We Charge for Onboarding Services?
5 Where Does Customer Advocacy Live?
Summary
Chapter 94 CEO‐to‐CEO Advice About the Customer Success Role
Signs It's Time to Hire Your First CCO
When a Fractional CCO Might Be Enough
What Does Great Look Like in a CCO?
Signs Your CCO Isn't Scaling
How I Engage with the CCO
Part Eight Product and Engineering
Chief Product Officer and Chief Technology Officer
Chapter 95 The Product Development Leaders
What I Look for in a Chief Product Officer. Scott Petry, co-founder and CEO, Authentic8
Chapter 96 Product Development Culture
Types of Development Cultures
Chapter 97 Technical Strategy: Proportional Engineering Investment and Managing Technical Debt
Chapter 98 Shifting to a New Development Culture
Things to Consider
Chapter 99 Starting Things
Things to Consider
Building an Initial Data Team for Your Startup. David Wilby, Former (at various times) Chief Product Officer, Chief Operating Officer, Chief Data Officer, Return Path
Chapter 100 Hiring Product Development Team Members
Interviewing
The Audition
The Practical Interview Process
Onboarding
Bootcamps
Chapter 101 Increasing the Funnel and Building Diverse Teams
Chapter 102 Retaining and Career Pathing People
Chapter 103 Hiring and Growing Leaders
Other Things to Consider
Chapter 104 Organizing, Collaborating with, and Motivating Effective Teams
Example 1: Quality
Example 2: Unified Product Development Organization
Example 3: Impedance Mismatch
Things to Consider
Chapter 105 Due Diligence and Lessons Learned from a Sale Process
People
Team
Product
System Overview
Privacy/Security
IP and Legal Risks
Costs
Risk Assessment
Chapter 106 Selling Your Company: Preparation
Preparation
Licenses and Intellectual Property
Privacy and Data Governance
Security
Product
Documenting Systems and Processes
Metrics
Costs
Chapter 107 Selling Your Company: Telling the Story
Conclusion
Chapter 108 CEO‐to‐CEO Advice About the Product/Engineering Role
Signs It's Time to Hire Your First Chief Product Officer
When a Fractional Chief Product Officer Might Be Enough
Signs It's Time to Hire Your First Chief Technology Officer
When a Fractional Chief Technology Officer Might Be Enough
What Does Great Look Like in a Chief Product or Technology Officer?
Signs Your Chief Product or Technology Officer Isn't Scaling
How I Engage with the Chief Product or Technology Officer
Part Nine Privacy
Chief Privacy Officer. The Rise of the Privacy Officer
Chapter 109 The Role of Privacy Officer
Chapter 110 Privacy Advice for Startups
Chapter 111 Legal Documents
Privacy Policy
Internal Privacy Policy
Terms of Service
Chapter 112 The European Union
Chapter 113 Data Mapping
Chapter 114 Data Breach
Chapter 115 Least Privileged Access
Chapter 116 Employee Training Engagement
Chapter 117 Building Your Privacy Team in a Startup
Chapter 118 Building Your Privacy Team as You Scaleup
Chapter 119 Certifications
Chapter 120 Assessments
Final Thoughts
Chapter 121 CEO‐to‐CEO Advice About the Privacy Role
Signs It's Time to Hire Your First CPO
When a Fractional Chief Privacy Officer Might Be Enough
What Does Great Look Like in a Chief Privacy Officer?
Signs Your CPO Isn't Scaling
How I Engage with the CPO
Part Ten Operations
Chief Operating Officer
Types of COOs
A Few Common Areas for the COO
Company Operating System
Managing the Marketing/Product/Sales Triangle
Metrics and Measurements
What I Look for in a Chief Operating Officer. Brad Feld. Foundry Group partner, Techstars co‐founder
Chapter 122 CEO‐to‐CEO Advice About the Operating Role
Complexity or Crutch?
Chapter 123 The Future of Executive Work
Welcome to the Executive Gig Economy
Chapter 124 Fractional Chief Financial Officer
The Need
The Structure
The Role
The Skills
The Exit
Chapter 125 Fractional Chief People Officer
Fractional HR Tasks
Startup or Established?
Transitions
Qualities of a Fractional HR Person
Chapter 126 Fractional Chief Marketing Officer
Fractional Opportunities for CMOs
Qualities of a Fractional CMO
Fractional Opportunities for Companies
Chapter 127 Fractional Chief Revenue Officer
Becoming a Fractional Executive
Finding Fractional Roles
Cautionary Advice
Chapter 128 Fractional Chief Revenue Officer
Qualities of a Fractional CRO
What to Expect as a Fractional CRO
The Good Part
Chapter 129 Fractional Chief Business Development Officer
Alignment
Objectives
Trust
Passion
Chapter 130 Fractional Chief Customer Officer
Things to Figure Out Quickly
Should You Pursue a Fractional Role?
Why Companies Need Fractional Executives
Chapter 131 Fractional Chief Product/Technology Officer
Getting Started in a Fractional Product Role
What Does a Fractional Product Person Do?
Advice for Companies
Final Thought
Chapter 132 Fractional Chief Privacy Officer
Qualities of a Fractional Privacy Officer
What a Fractional Privacy Officer Does
Advice for Companies
Conclusion
Epilogue
References
Acknowledgments
About the Authors
Contributors
Index
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