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

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  • Edition: 1st
  • Format: Hardcover
  • Copyright: 2021-06-09
  • Publisher: Wiley

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One of the greatest challenges for startup teams is scaling because usually there's not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. Matt Blumberg and his team understand the scaling challenges—they've been there, and it took them nearly 20 years to scale and achieve a successful exit.  Along the way they learned what worked and what didn’t work, and they share their lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a "CEO to CEO Advice" summary from Blumberg on what great looks like for that CXO, signs your CXO isn't scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career."
—Scott Dorsey, Managing Partner, High Alpha

Author Biography

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

Table of Contents


Scott Dorsey



1 The Nature of a CXO’s Role

2 Scaling a CXO


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


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


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


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


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


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


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


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


Chief Operating Officer

Jack Sinclair

122 CEO-to-CEO Advice


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



Pete Birkeland



About the Authors



Supplemental Materials

What is included with this book?

The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any access cards, study guides, lab manuals, CDs, etc.

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