Bill Macaitis offers board advisory services where he shares his cumulative go-to-market knowledge leading marketing for the three fastest-growing SaaS companies in history: Slack (CRO/CMO), Zendesk (CMO), and Salesforce (SVP Marketing). He has achieved 5 exits over his career. Bill now enjoys helping other companies achieve hyper-growth by developing cutting edge marketing strategies, helping them build out their own world-class marketing team, and implementing modern marketing tech stacks.

On This Episode:

• Bill talks about how optimism plays a role in his business success.
• Learn the importance of automation.
• Hear the story of Bill’s first start-up.
• Get secrets to branding a B2B company.
• Learn how to develop helpful metrics for your team. Chris and Bill discuss how to stay innovative without waiting to move forward.

Key Takeaways

1. 1. The marketing playbook is always evolving.
   2. Infuse personality into your products to create an emotional bond with your customer. Don’t be afraid to have fun.
   3. Money is not as important as the mission.

Tweetable Quotes:

• “Your brand goes way beyond your logo.”
• “The lid of your success is you.”

Since 2019, Elisa Steele has served as Chair, Board of Directors at Namely, Inc., a financial and human capital management software company, where she served as Chief Executive Officer from 2018 to 2019. Ms. Steele previously served as Chief Executive Officer and President of Jive Software, Inc., a collaboration software company, which was acquired in June 2017. Ms. Steele was a member of the Jive Software executive leadership team since 2014. Prior to joining Jive Software, Ms. Steele served as Chief Marketing Officer and Corporate Vice President, Consumer Apps & Services at Microsoft Corporation, a worldwide provider of software, services and solutions, and Chief Marketing Officer of Skype, an Internet communications company, from 2012-2014. Ms. Steele also has held executive leadership positions Yahoo! Inc. and NetApp, Inc. Ms. Steele has served as a member of the board of directors of Cornerstone OnDemand, Inc., a learning and human capital management software company, since 2018. Ms. Steele holds a B.S. from the University of New Hampshire and an M.B.A. from San Francisco State University.

On This Episode:

• Learn the belief systems that Elisa has carried through her career.
• Find out how sales helped Elisa get hooked on the idea of impact.
• Discover the keys to creating a solid product for your customer.
• Get tips regarding how to pivot.
• Elisa explains what you should takeaway from failure.

Key Takeaways

1. 1. Develop a broad collection of experiences in life and business.
   2. Don’t be afraid to innovate in uncharted territory.
   3. Build an advisory board around you.

Tweetable Quotes:

• Good leaders respect and admire the talents in their people.
• If you don’t have a diverse team, you’re not going to perform at your top performance.
• Be yourself and be okay with that.
• Marketing is about influence.

Andrew co-founded Outreach in 2014 and served as VP of Product Strategy. He began his career in design, working for agencies in the Bay Area until 2009 when he moved to Seattle and transitioned to designing product at Pelago. He has since left his role at Outreach and is now working on solving problems in climate change.

He is driven by the idea that certain technologies will significantly move our society forward, and that if we can simply dream of the future, we can work our way backward from that dream and find our path forward. He is also a passionate believer in setting exceptionally high bars, and working to find a way to reach them. He holds a BFA from the California College of Design and lives in Seattle with his wife and his adorable (but spoiled) dog Cody.

On This Episode:

• Andrew and Chris go back before the genesis of Outreach and the failed venture that led them there.
• Learn how to pivot from failure.
• Andrew explains how to become a successful product owner.
• Learn common pitfalls when trying to serve your customer base.

Key Takeaways

1. 1. Take time to look at the data from your failures.
   2. Test really rough ideas as soon as possible to see if there is interest.
   3. Know when to pivot.

Tweetable Quotes:

• "You want strong visceral reactions."

• "Nobody pays for a hammer, they pay for what a hammer gets you."

Quentin was CTO of Dropbox, a company that’s brought millions of consumers, teams, and business onto the cloud. As CTO, he was integral to taking the company public, leading the engineering, product, design, and growth teams throughout the process. Quentin also helped broaden the company’s portfolio with the HelloSign acquisition and the recent launch of their new team-oriented collaboration product, Dropbox Spaces.

Prior to Dropbox, Quentin spent nearly two decades with Microsoft, starting as a software engineer, then product manager, and eventually leading the entire family of data products — from Microsoft SQL Server, the BI products, no-SQL, and ML capabilities on-prem and in Azure. After Microsoft, Quentin joined SAP and helped to build the company’s growth strategy, first as their CTO, then leading strategy, corpdev, M&A and strategic partnerships. As a part of that role, he helped SAP spin-up an emerging business unit with a venture mindset for working directly with the startup community.

On This Episode:

• Learn how crucial a clear vision is to your career path.
• Discover the importance of becoming. self-aware of your own limitations.
• Hear the key philosophies to building high-performing teams.
• Get a few helpful interview questions to ask potential team members.
• Quentin shares how he chooses what founders he makes bets on.

Key Takeaways

To be a full-stack leader you must possess the following qualities:

1. 1. Vision
   2. Strategy
   3. Leadership
   4. Management
   5. Technical Accuity
   6. Business Accuity

Tweetable Quotes:

• It’s very easy to mask people dysfunction with short-term success.

Dr. Pantas Sutardja is founder, president and CEO of Latticework.

A legend in the storage industry, Dr. Sutardja has over 25 years of experience in the storage and semiconductor industry. He began his career at IBM Almaden Research Center where he developed the company’s first CMOS read channel chip. Dr. Sutardja and his brother would eventually team up to create Marvell Technology Group Limited in 1995, turning a startup into a publicly traded global leader in storage with several billion storage chips sold to date.

Now, Dr. Sutardja has turned his storage sights to the hybrid cloud with Latticework leading the development of hybrid cloud-edge solutions to meet consumer demand for more storage and bandwidth related to skyrocketing data and video usage. The company’s first product, Amber, is the first personal storage device that provides consumers with security and privacy not available in public offerings.

In his personal life, Dr. Sutardja is a noted philanthropist, establishing the Sutardja Center for Entrepreneurship & Technology at UC Berkeley, and, with his wife, creating a private foundation with an initial focus on education and medical fields.

Dr. Sutardja holds BS, MS and PhD degrees in Electrical Engineering and Computer Sciences from University of California, Berkeley.

On This Episode:

• Learn how to turn your hobby into a career.
• Pantas trajects the abnormal trajectory of his career from childhood onward.
• Discover the power of a challenge.
• Chris and Pantas define what it means to work hard.

Key Takeaways

1. Having a cushion when you start your first business is incredibly valuable.
2. When someone says, “you can’t do it” let that be a challenge.
3. Your team must have authentic confidence in themselves.

Tweetable Quotes:

• “Management has to lead by example.”
• “Your culture is a summation of your behaviors.”

Tracy leads the people experience programs at Zenefits including employee engagement, compensation, benefits, learning and development, employee relations, talent acquisition, and employment branding. Prior to Zenefits, she held HR leadership roles at Genesys, MobiTV, Inc., and Organic Inc. Passionate about the impact of inclusive business cultures, she taught at San Francisco State University for over 10 years, where she demystified human resources management for newcomers to the field. Tracy holds a bachelor’s degree in English from Sonoma State University. Holding a bachelor’s degree in English from Sonoma State University, Tracy was also a member of the faculty at San Francisco State University where she demystified human resources management for newcomers to the field for over 10 years.

On This Episode:

• Learn how HR has changed due to the pandemic
• Discover the best ways to keep communication open when working remotely.
• Tracy explains what companies should look for in leaders.

Key Takeaways

1. Work is no longer about where you go, it’s what you do and who with.
2. How you incentivize people is important, be mindful of how you reward your team.
3. Hire people who have a predisposition to your values.

Tweetable:

• “Your either a builder, an optimizer, or a maintainer.”
• “Don’t just hire for the job, hire for the team.”

Blair Shane is currently Partner & CMO at Sequoia Capital where she leads a team focused on helping founders build legendary companies. Her experience makes her well suited to helping a partnership and portfolio made up of diverse, intelligent and driven individuals drive results. Prior to Sequoia, Blair was CMO & Associate Dean of Stanford Graduate School of Business, where she revitalized its marketing function. She joined Stanford from the California Academy of Sciences where, as CMO, she re-opened the museum in 2008 and launched new programs such as NightLife and variable pricing to rejuvenate attendance. Before that, Blair spent seven years at Charles Schwab where she was VP of marketing planning and integration. In whatever job she is in, Blair is passionate about creating new possibilities and getting what may be perceived as impossible done.

On This Episode:

• Learn the qualities that you should adopt to be successful.
• Discover how to take your product to market and ensure it's well-received.
• Chris and Blair define the difference between brand marketing and performance marketing.
• Blair describes her own evolution.

Doug Winter is the co-founder and CEO of Seismic, a unicorn SaaS company valued at over $1B based out of San Diego, CA. Prior to Seismic, Doug also successfully built and sold his last company, Objectiva Software Solutions, for $90M. 

Key Points:

• How Doug decided that Seismic was an idea worth going "all in" on. 
• How to build a foundation that scales
• How Doug and his co-founders approached built a high performing company culture
• The most important keys to raising capital (and if you should)
• Leadership Do's and Don'ts based on Doug's experience building numerous companies

Key Quotes:

• "At some point, you gotta be a little bit stupid and just go for it."
• “Get customer validation early and often." 
• "You can build an incredible product, but if you don't know how to sell it, don't know how to take it to market, no one is ever going to know about it."
• "If you don't know who your first ten customers could be or should be, then you probably haven't thought through things enough..."

Doug Winter

https://seismic.com/

About Scot Chisholm:

Scot is the CEO & Co-Founder of Classy, a social enterprise that creates world-class online fundraising software for nonprofits, modernizing the giving experience to accelerate global social impact. Since 2011, thousands of nonprofits have collectively raised nearly two billion dollars on the Classy platform, tackling social and environmental issues of every kind. 

Scot co-founded Classy when one of the largest cancer organizations in the country refused to accept the money he raised during a fundraising pub crawl held to honor his mom, a two-time breast cancer survivor. Scot was inspired to start Classy to make it easier for anyone to support a cause that’s meaningful to them, while at the same time making it easier for organizations to make lasting connections with the next generation of supporters. Based in San Diego, CA, Classy has over 200 employees and has raised $40 million to-date in growth capital from prominent technology investors, including Mithril Capital Partners, Salesforce Ventures, Hinge Capital and Bullpen Capital. Classy is well known for its company culture and social enterprise business model that includes the Classy Awards, now the largest social impact award show in the country, its early support of the Pledge 1% movement, and its employee giving program called #ClassyGives. Most recently, Classy was recognized as a Glassdoor Best Place to Work, San Diego Union-Tribune Top Workplace and Entrepreneur Best Company Cultures.

Scot’s recent recognitions include Glassdoor as a “Top CEO in the United States”, San Diego Business Journal as one of the “40 Next Top Business Leaders Under 40” and the “500 Most Influential Business Leaders in San Diego”, and Businessweek as one of the “Top 5 Most Promising Social Entrepreneurs.” Scot currently serves on the Leadership Council for the California Nature Conservancy, on the Board of Directors at Street Soccer USA and ASC San Diego and on the Advisory Board at Team Rubicon, having previously served a four-year term on the founding Board of Directors. Scot is also an active investor, investing out of a fund called Tall Timbers that includes public and private investments with a focus on SaaS and socially responsible businesses.

Scot is a frequent speaker on social entrepreneurship, trends in giving, and the journey of scaling a startup-for-good. Past speaking appearances include Amazon’s Imagine A Better World Conference; TEDx; Dreamforce; SaaStr; Collision; SOCAP; AFP; Nonprofit Technology Conference (NTC); and Inbound.

Prior to Classy, Scot worked at Booz Allen Hamilton and helped create and lead their Lean Six Sigma practice on the west coast. Scot received a Bachelors of Science in Mechanical and Industrial Engineering from the University of Massachusetts, Amherst.

On This Episode:

• Learn how Classy went from a passion project to full-fledged business.
• Hear how to create and market your product offering.
• Discover the way to create a culture that scales.
• Find out what early-stage entrepreneurs MUST get right from the beginning.

About David Fano:

I am a serial entrepreneur and senior leader known for building high growth teams. Most recently I served as Chief Growth Officer of WeWork, where I was responsible for driving their rapid expansion and as a result increasing revenue 100% year-over-year for 4 consecutive years to a $4 billion annual run rate. Trained as an architect, my interests and expertise lie in connecting technology and data to help people work. Working cross functionally , I enable new insights into the knowledge management of technology, and develop approaches that leverage data to deliver value and drive business performance. I received his Master of Architecture with honors from Columbia University and was an Adjunct Professor at Columbia University's GSAPP from 2006 - 2012. I have led seminars and workshops focusing on the impact of technology on design processes at conferences such as Autodesk University, RTC North America and AIA's Technology in Architectural Practice. 

On This Episode:

• David shares his background in architecture and why he got disenchanted with the industry.
• Learn how David quickly scaled to $4 BILLION.
• Find out the keys to building a high performing team.

Key Takeaways:

1. Make sure you don’t expand to quickly into other products. Focus on your blue ocean.
2. When it comes to leading a team, you must have a combination of autonomy and structure.
3. Just because something worked a certain way today doesn’t mean it will work the same way tomorrow.

Tweetable Quotes:

• “Every level is a new devil.”
• “Systematically build empathy.”
• “You don’t have an awesome career by yourself.”
• “The answer doesn’t have to be ‘start a company.’”