Startup CXO A Field Guide to Scaling Up Your Company's Critical Functions and Teams

Startup CXO is the definitive book for any executive of any C-suite executive or function within a high-growth company. While the heads of sales, product, HR, and other functional teams inside big companies are usually groomed for the job for years, startup executives aren't. They are often young and relatively inexperienced in business in general. Author Matt Blumberg, a technology and marketing entrepreneur, knows this all too well. His first book, Startup CEO (now on its Second Edition) was the fifth book in the Startup Revolution series, was largely based on his experience starting, running, building, and ultimately selling a technology company called Return Path, which later became the driving force behind the creation of his blog, OnlyOnce - because "you're only a first time CEO once." 

Now, Blumberg has gotten his former executive team (many of whom are working with him as co-founders of his new venture, Bolster. In Startup CXO, they share  their collective wisdom of how to build and scale the different functions inside a successful high growth company. The book is a sharp resource covering hundreds of issues that their team faced in collectively more than 100 years serving as senior executives in startups. The book:

• �Offers valuable insights into how functional leaders set the vision and strategy for their departments in conjunction with the rest of the executive team and drives that strategy through to execution
• �Gives specific growth playbooks for each department, from things like “how to avoid technical debt” to “how to set sales comp plans” to “how to scale your culture and values”
• �Examines how a functional leaders must align available resources with their strategy in order to ensure success
• �Addresses what it takes to master the "How" of being a CXO - from leading a team to managing in any type of market

Engaging and informative, this book is essential reading for any, and every, CEO and C-level executive inside any growing company.

MATT BLUMBERG is founder and CEO of Bolster, an on-demand executive talent marketplace to help startup CEOs scale their leadership team, themselves, and their board. He was the founder and CEO of Return Path and is the author of Startup CEO, and the blog, StartupCEO.com. He lives in New York with his wife and three children.

PETER M. BIRKELAND is a sociologist, author, and writer who helps people turn ideas into books. www.peterbirkeland.com

Foreword

Scott Dorsey

PART 1 INTRODUCTION

Introduction

1 The Nature of a CXO’s Role

2 Scaling a CXO

PART 2 FINANCE

Chief Financial Officer

Jack Sinclair

3 In the Beginning: Laying the Foundation

4 Fundraising

5 Size of Opportunity

6 Financial Plan

7 Unit Economics and KPIs

8 Investor Ecosystem Research

9 Pricing and Valuation

10 Diligence and Corporate Documentation

11 Using External Counsel

12 Operational Accounting

13 Treasury and Cash Management

14 Building an In-house Accounting Team

15 International Operations

16 Strategic Finance

17 Other Areas to Partner With

18 High Impact Areas for the Startup CFO as Partner

19 Board and Shareholder Management

20 Equity

21 Mergers and Acquisitions (M&A)

22 Bonus Section: What We Used for Our Internal Systems When We Started Bolster

23 CEO-to-CEO Advice

PART 3 PEOPLE

Chief People Officer

Cathy Hawley

24 Values and Culture

25 Diversity, Equity, and Inclusion (DE&I)

26 Building Your Team

27 Organizational Design and Operating Systems

28 Team Development

29 Leadership Development

30 Talent and Performance Management

31 Career Pathing

32 Role-Specific Learning and Development

33 Employee Engagement

34 Rewards and Recognition

35 Reductions in Force

36 Recruiting

37 Onboarding

38 Compensation

39 People Operations

40 Systems

41 CEO-to-CEO Advice

PART 4 MARKETING

Chief Marketing Officer

Nick Badgett and Holly Enneking

42 Where to Start

43 Generating Demand for Sales

44 Supporting the Company Culture

45 Breaking Down Marketing’s Functions

46 Events

47 Content and Communications

48 Product Marketing

49 Marketing Operations

50 Sales Development

51 Marketing as a Partner/Collaborating with the Rest of the C-Suite

52 Building a Marketing Machine (Scaleup)

53 CEO-to-CEO Advice

PART 5 SALES

Chief Revenue Officer

Anita Absey

54 In the Beginning: From Prospect to Customer

55 Hiring the Right People

56 Profile of Successful Salespeople

57 Some Myth Busting

58 Compensating Sales Team Members

59 Pipeline

60 Scaling the Sales Organization

61 Scaling Your Team Through Culture

62 Scaling Sales Process and Methodology

63 Scaling the Operating System

64 Marketing Alignment

65 Market Assessment and Alignment

66 Expanding Distribution Channels

67 Geographic Expansion

68 Pricing and Packaging

69 CEO-to-CEO Advice

PART 6 BUSINESS DEVELOPMENT

Chief Business Development Officer

Ken Takahashi

70 How to Make the Biggest Impact as a CBDO

71 Building Your Influence Internally

72 Building Your Influence Externally

73 Where Internal and External Meet: Your Relationship with Your CEO

74 Influence Meets Operating System

75 Develop External Trust for the Company

76 Build Your Influence in Strategy

77 Building Your Influence in Business Development

78 When Things Go Wrong in a Partnership...and They Will

79 Geographic Expansion

80 M&A: Buy Side

81 M&A: Sell Side

82 CEO-to-CEO Advice

PART 7 CUSTOMERS

Chief Customer Officer

George Bilbrey

83 Five Misperceptions

84 Startup Customer Success Organization

85 Scaling the Service Organization

86 Timing: When to Hire Your Team

87 Customer Segmentation and Journey

88 Understanding Customers

89 Understanding Customers Through Metrics

90 Foundations of a Great Customer Service Organization

91 Building an Effective Team

92 Partnering with the Organization

93 Five Eternal Questions

94 CEO-to-CEO Advice

PART 8 PRODUCT

Chief Technology Officer and Chief Product Officer

Shawn Nussbaum

95 The Product Development Leaders

96 Product Development Culture

97 Technical Strategy: Proportional Engineering Investment and Managing Technical Debt

98 Shifting to a New Development Culture

99 Starting Things

100 Hiring Product Development Team Members

101 Increasing the Funnel and Building Diverse Teams

102 Retaining and Career Pathing People

103 Hiring and Growing Leaders

104 Organizing, Collaborating with, and Motivating Effective Teams

105 Diligence and Lessons Learned from a Sale Process  

106 Selling Your Company

107 Telling the Story

108 CEO-to-CEO Advice

PART 9 PRIVACY

Chief Privacy Officer

Dennis Dayman

109 The Role of Privacy Officer

110 Privacy Advice for Startups

111 Legal Documents

112 The European Union

113 Data Mapping

114 Data Breach

115 Least Privileged Access

116 Employee Training Engagement

117 Building Your Privacy Team in a Startup

118 Building Your Privacy Team as You Scale Up

119 Certifications

120 Assessments

121 CEO-to-CEO Advice

PART 10 OPERATIONS

Chief Operating Officer

Jack Sinclair

122 CEO-to-CEO Advice

PART 11 THE FUTURE OF FRACTIONAL EXECUTIVE WORK

123 The Future of Executive Work

124 Fractional Chief Financial Officer

John McCarthy

125 Fractional Chief People Officer

Courtney Graeber

126 Fractional Chief Marketing Officer

Scott Kabat

127 Fractional Chief Revenue Officer

B.J. Bushur

128 Fractional Chief Revenue Officer

Sherri Sklar

129 Fractional Chief Business Development Officer

Jon Guttenberg

130 Fractional Chief Customer Officer

Amy Mustoe

131 Fractional Chief Product/Technology Officer

Drew Dillon

132 Fractional Chief Privacy Officer

Teresa Troester-Falk

Conclusion

Epilogue

Pete Birkeland

References

Acknowledgments

About the Authors

Appendix

Index