It's imperative to determine that you will have a good working relationship, and share the same values with a CEO, well before you take a board seat. Karen Appleton Page was employee number seven at Box and her role evolved with the booming business over her nine year tenure. When she began seriously exploring board opportunities this year, she realized that having the right chemistry with the CEO, much like she had with Aaron Levie at Box, would be key in finding the right fit. In this episode, learn how Karen broke boundaries as the first Industry GTM leader at Box and about her recent journey to Deputy's board.

Jenny Cheng led product program management at Salesforce during their explosive growth period from 2002 to 2011. Today she is an executive at PayPal focused on the intersection between the customer and the product. Learn what she did when she decided to get serious about joining boards, why she chose to be on the board of a smaller startup vs. a large public company and how to balance a board seat with your day job.

Steve Collins and Bill Conroy both sit on Instructure's (NYSE: INST) board among many others including Shopify, MuleSoft, etc. Steve has had a successful career as CFO (ExactTarget) and Bill with a focus in sales earlier on and CEO (Initiate Systems, acquired by IBM) later in his operator career. With distinctive skill sets, they naturally had different paths to the board room, but their messages around finding the stage of growth that is best suited for you are quite similar. Listen as they give advice on when it's the right time to join a board and how to play on your strengths as an effective Director.

Anita Sands has spent much of her career in the financial services industry including leadership roles at UBS, Citigroup and RBC. She currently resides on the boards of Symantec, ServiceNow and Pure Storage as well as advisory positions at Accompany, Thrive Global and Docusign. Anita has helped many businesses reach new levels with her strategic insight. Learn how to not only get on your first board, but navigate the position as a new board member. Also listen as Anita explains the importance of selecting the right board members and using them as a strategic assest for your company.

Caroline Tsay wanted to be a neurosurgeon when she grew up. Plans changed! Caroline has held leadership positions at Yahoo and HPE and is currently the CEO of Compute Software. She also sits on the board of Coca-Cola, Rosetta Stone and Morningstar. So how did this all come to be? In 2013, her boss introduced her to an executive coach that pushed her to build her own brand and explore board opportunities. In this episode, Caroline gives key insights on leveraging your network to find board seats, how board positions can make you a better leader and advice for executives looking to join their first board.

Elisa Steele is currently the CEO of Namely and holds board positions at Cornerstone OnDemand (Chair) and Splunk as well as advisor roles at People.ai and Tile. Her past CMO experiences at Yahoo, Skype and Microsoft naturally led her to explore board seats where she could add her expertise and perspective. Learn how leadership teams can and should use their board as a resource, how roles differ on a board, the importance of using your network to explore opportunities and how to establish your voice on the board.

A Chief People Officer may not be the first choice to add to a board, but it is a choice that all early stage startups should make from the very beginning. Marty Reaume, Chief People Officer at Twilio, has help multiple HR and People positions at companies like NetSuite and Fitbit. She also holds board positions at Ambra Health and SPS Commerce. Marty explains the importance of hiring HR and People talent early on in a business and key initiatives that are currently top of mind as the CPO at Twilio. She also explains when she started to get serious about joining a board and advice for a CEO building out her board for the first time.

Bill Welch was most recently the President & COO of Duo Security, guiding them through a successful sales to Cisco. He's also held key leadership roles at Zscaler (which went public in early 2018), Hewlett-Packard and Symantec and most recently took an independent board seat at Logikcull. Bill explains the importance of hiring the right individuals for your company and making sure everyone has a role in the journey (employees, customers, partners, etc.). He also explains how he explored board opportunities and the power of board mentors in your company.

John True has had an impressive career, both as an operator and as a board member. He is currently a GP at Cultivation Capital and has previously held leadership positions at Guidewire Software, Fortify Software and EqualLogic as well as numerous board positions. John takes us through his remarkable career, including his experience joining his first board and what he's learned from his (currently) 7 board seats. He also discusses the importance of devoting time to building relationships so you're top of mind when opportunities come about and how to make the biggest impact once you get a seat at the table.

Bill Wagner started his tenure at LogMeIn in 2013 as their first-ever Chief Operating Officer. In 2015 he was promoted to President & CEO and joined the board shortly after where he's played a key role in their rapid growth. Prior to LogMeIn, he was COO at Vocus, a cloud-marketing software company, and held multiple executive and operator roles prior to that. Bill discusses the largest drivers of growth when he joined LogMeIn, the philosophy behind their freemium model and his role on the board when he first started his tenure. Bill also explains how to get the most leverage out of the board, the importance of a diverse board that brings different experiences to the table, and how to search for key external board members.

Jim Baum is currently a Venture Partner at OpenView and serves on multiple boards including Logz.io, Applitools, project44 and DataStax. Jim previously served as President and CEO of Netezza where he drove the nearly $2B acquisition of Netezza by IBM in 2010. Jim also led Endeca’s early rise from tiny startup to the leading provider of innovative information access and delivery software solutions. Prior to Endeca and Netezza, he served at PTC as an Executive Vice President and General Manager. On this episode, Jim discusses his experience as a venture partner and the difference between joining a board as an investor vs. an independent board member, why sitting on a board is a great opportunity for executives and advice for expansion stage CEOs looking for the right board members.

We're taking a break in between seasons to chat with Lessonly's CEO, Max Yoder. Max discusses the background behind his new book, Do Better Work, and how the principles laid out in the book are integrated throughout the Lessonly organization. Learn more and preorder your copy by going to www.dobetter.work.