OpenView

Entering a company as a new CEO can be intimidating. It’s important to set the tone while also respecting the existing culture. Alex Shootman shares his personal experience on stepping into the role as Workfront's CEO.

Setting the Tone as a New CEO

Alex MacCaw is the founder of Clearbit and Reflect, and his journey with each company has been wildly different. Clearbit took more of a “classic” startup approach—raising VC money, hiring hundreds of people, and working from an office in SF.&nbsp; In 2020, he charted a new course by replacing himself as CEO at Clearbit, selling all his possessions and living full-time on a sailboat in the Atlantic. And now he’s building his new company Reflect in with a totally different approach —building a fully remote &amp; asynchronous “lifestyle” company that decidedly eschews VC money and the other common hallmarks of a tech startup.&nbsp; Alex shares everything he’s learned as a founder and why he believes building startups should not be one-size-fits-all. Blake and Alex talk through: (7:07) Pros/Cons of being asynchronous by design(09:01) Why Alex doesn’t believe in remote work for large companies(10:11) Remote work pitfalls(14:21) When to replace yourself as CEO(15:52) How to find your zone of genius(18:31) When do startups hire a CFO or COO?(21:14) #1 piece of advice for founders(24:14) Things to know before you found a startup (B2B vs. B2C)(27:27) Why not raise venture capital(28:28) When startups should (or shouldn’t) raise venture capital(29:40) How Reflect started crowdfunding(39:14) What AI and ChatGPT is good for(44:13) Best time to start a company(46:20) Not all startups need VC funding(47:16) Advice for VCs from a founder

2x startup founder behind Clearbit and Reflect. Clearbit is a B2B data enrichment API for sales & marketing teams. Reflect is a B2C note-taking or notes app for anyone.

Alex MacCaw

Founder, CEO at Reflect

Alex MacCaw is the founder of Clearbit and Reflect, and his journey with each company has been wildly different. Clearbit took more of a “classic” startup approach and now he’s building his new company Reflect in with a totally different way—building a fully remote & asynchronous “lifestyle” company that decidedly eschews VC money and the other common hallmarks of a tech startup. Alex shares everything he’s learned as a founder and why he believes building startups should not be one-size-fits-all.


Alex MacCaw (Clearbit & Reflect): Everything I’ve Learned as Startup Founder

Patrick says work-life balance is the wrong framework. It’s more about work-life fit and finding what suits you best. This is especially true for startup founders, where your work is often all-consuming. Episode Highlights<ul><li>[00:32&nbsp;-&nbsp;02:30] Thoughts on work/life balance</li></ul> Mentioned in this episode:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a>Connect with Patrick on <a href="https://www.linkedin.com/in/patrickccampbell/" rel="noopener noreferrer" target="_blank">LinkedIn</a>Follow Patrick on <a href="https://twitter.com/Patticus?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor" rel="noopener noreferrer" target="_blank">Twitter</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

Patrick Campbell is the CEO of ProfitWell (formerly Price Intelligently), the software for helping subscription companies with their monetization and retention strategies. ProfitWell also provides free turnkey subscription financial metrics for over eight thousand companies. Prior to ProfitWell, Patrick lead Strategic Initiatives for Boston based Gemvara and was an Economist at Google and the US Intelligence community.

Patrick Campbell

Patrick says work-life balance is the wrong framework. It’s more about work-life fit and finding what suits you best. This is especially true for startup founders, where your work is often all-consuming.



Patrick Campbell (ProfitWell): Work-Life Balance for Founders

Culture at a startup is always tricky, but there’s one common mistake founders should avoid at all costs. It’s the desire to make everyone happy all the time. Patrick says this leads to a “culture of accommodation” which ultimately ends up not working for anyone. Hear Patrick’s journey as a founder to define the culture at ProfitWell, and how you can do the same at your startup. Episode Highlights<ul><li>[00:03&nbsp;-&nbsp;01:31] Episode intro: Patrick Campbell</li><li>[01:59&nbsp;-&nbsp;04:04] What is the role and importance of company culture in today's market environment?</li><li>[06:39&nbsp;-&nbsp;10:26] The culture of ProfitWell and the journey to get there</li><li>[12:15&nbsp;-&nbsp;16:26] The most charitable interpretation</li><li>[17:23&nbsp;-&nbsp;20:08] ProfitWell values and four principles</li><li>[20:21&nbsp;-&nbsp;23:16] Speaking their mind, being human in the most charitable way</li><li>[21:11&nbsp;-&nbsp;23:16] Values and principles must have trade-offs</li><li>[23:16&nbsp;-&nbsp;25:41] Here's how we operate, transparency in hiring</li><li>[25:46&nbsp;-&nbsp;32:10] Advice for making culture something more than theoretical, a real experience</li></ul> Mentioned in this episode:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a>Connect with Patrick on <a href="https://www.linkedin.com/in/patrickccampbell/" rel="noopener noreferrer" target="_blank">LinkedIn</a>Follow Patrick on <a href="https://twitter.com/Patticus?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor" rel="noopener noreferrer" target="_blank">Twitter</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

CEO of ProfitWell

Culture at a startup is always tricky, but there’s one common mistake founders should avoid at all costs. It’s the desire to make everyone happy all the time. Patrick says this leads to a “culture of accommodation” which ultimately ends up not working for anyone. Hear Patrick’s journey as a founder to define the culture at ProfitWell, and how you can do the same at your startup.


Patrick Campbell (ProfitWell): What’s the “Right” Culture for Your Company?

Every startup wants to create a category. This is often a mistake. Or at least it’s prioritized too early by many founders and marketers. Ryan Carlson, longtime CMO at Okta, explains why this falls flat with customers and what to do instead. Key Takeaways: <ul><li>[00:31&nbsp;-&nbsp;01:53] &nbsp;A noted skeptic on category creation</li><li>[01:54&nbsp;-&nbsp;02:15] Everybody wants to be a category creator</li><li>[02:16&nbsp;-&nbsp;03:19] Focus on how they're better than the alternative</li></ul> Mentioned in this episode:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a><a href="https://www.linkedin.com/in/ryancarlson/" rel="noopener noreferrer" target="_blank">Ryan Carlson, Chief Marketing and Strategy Officer at Wiz</a><a href="https://www.linkedin.com/in/ryancarlson/" rel="noopener noreferrer" target="_blank">LinkedIn</a><a href="https://twitter.com/ryantcarlson?lang=en" rel="noopener noreferrer" target="_blank">Twitter</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

I love technology products, and building the companies who make them.

Ryan Carlson

Chief Marketing and Strategy Officer at Wiz

Every startup wants to create a category. This is often a mistake. Or at least it’s prioritized too early by many founders and marketers. Ryan Carlson, longtime CMO at Okta, explains why this falls flat with customers and what to do instead.


Ryan Carlson (ex-Wiz, Okta): Category Creation is Overrated

Okta’s CMO for 5+ years, Ryan Carlson, says marketing’s guiding light should be the company mission and values. Marketing’s job is to tell the story of the company, not to merely promote the product or drive leads into the top of a funnel. Authentic marketing is rooted in the BIG questions. Why does this company exist? Who should care about that and why?Today’s episode will help you:<ul><li>Understand this strategic approach to marketing</li><li>See the impact strategic marketing has on your audience</li><li>How to hire mission/values-aligned marketers</li><li>Leverage Ryan’s playbook for company storytelling by working directly with customers</li></ul> Key Takeaways: <ul><li>[00:19&nbsp;-&nbsp;03:37] Introduction to Ryan Carlson, and thoughts on company culture in the world of marketing</li><li>[03:44&nbsp;-&nbsp;06:53] What should define culture is the mission, values, and vision</li><li>[06:54&nbsp;-&nbsp;10:00] Imparting importance, and showing why culture mattered at Okta</li><li>[10:02&nbsp;-&nbsp;13:32] Authenticity, avoiding hyperbole and marketing BS</li><li>[13:43&nbsp;-&nbsp;16:10] Who do you hire to marketing leadership to operate more authentically?</li><li>[16:13&nbsp;-&nbsp;18:18] Hiring true believers, and avoiding a "customer's wrong" mentality with product market fit</li><li>[19:26&nbsp;-&nbsp;22:45] Understanding why people like the product and the people behind it</li><li>[22:48&nbsp;-&nbsp;25:40] Combining pen to paper with mission, values, and vision</li><li>[25:42&nbsp;-&nbsp;28:27] Storytelling and presentations, how they impact retention</li><li>[28:30&nbsp;-&nbsp;32:26] Story and history of your company is different</li><li>[32:32&nbsp;-&nbsp;35:37] Figuring out if a company operates by its values as a candidate</li></ul> Mentioned in this episode:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a><a href="https://www.linkedin.com/in/ryancarlson/" rel="noopener noreferrer" target="_blank">Ryan Carlson, Chief Marketing and Strategy Officer at Wiz</a><a href="https://www.linkedin.com/in/ryancarlson/" rel="noopener noreferrer" target="_blank">LinkedIn</a><a href="https://twitter.com/ryantcarlson?lang=en" rel="noopener noreferrer" target="_blank">Twitter</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

Okta’s CMO for 5+ years, Ryan Carlson, says marketing’s guiding light should be the company mission and values. Marketing’s job is to tell the story of the company, not to merely promote the product or drive leads into the top of a funnel. Authentic marketing is rooted in the BIG questions. Why does this company exist? Who should care about that and why?


Ryan Carlson (ex-Wiz, Okta): Company Values = Marketing Message

Okta’s CMO for 5+ years, Ryan Carlson, says marketing’s guiding light should be the company mission and values. Marketing’s job is to tell the story of the company, not to merely promote the product or drive leads into the top of a funnel. Authentic marketing is rooted in the BIG questions. Why does this company exist? Who should care about that and why?Today’s episode will help you:
Understand this strategic approach to marketing
See the impact strategic marketing has on your audience
How to hire mission/values-aligned marketers
Leverage Ryan’s playbook for company storytelling by working directly with customers



Raj says that most of the PLG advice out there today is missing a key foundational point: data. Many PLG companies still rely on traditional sales &amp; marketing software that keeps data in silos. The key to winning in PLG starts with your data infrastructure, and wiring it up early helps you scale later. Mentioned in this episode:<a href="https://openviewpartners.com/newsletter/#.YfRAM-rMIuU" rel="noopener noreferrer" target="_blank">Sign up for OpenView's weekly newsletter</a><a href="https://www.linkedin.com/in/rajsarkar/" rel="noopener noreferrer" target="_blank">Raj Sarkar, CMO &amp; Advisor</a><a href="https://www.linkedin.com/in/rajsarkar/" rel="noopener noreferrer" target="_blank">LinkedIn</a><a href="https://twitter.com/rajsarkar?ref_src=twsrc%5Egoogle%7Ctwcamp%5Eserp%7Ctwgr%5Eauthor" rel="noopener noreferrer" target="_blank">Twitter</a>Subscribe to&nbsp;<a href="https://www.youtube.com/channel/UCaVvQTEaCyt2bbkoAh7wPyg" rel="noopener noreferrer" target="_blank">Blake Bartlett on YouTube</a>.Podcast produced by&nbsp;<a href="https://openviewpartners.com/" rel="noopener noreferrer" target="_blank">OpenView</a>.View our&nbsp;<a href="https://openviewpartners.com/blog" rel="noopener noreferrer" target="_blank">blog&nbsp;</a>for more context/inspiration.<a href="https://www.linkedin.com/company/openview-/" rel="noopener noreferrer" target="_blank">OpenView on Linkedin</a><a href="https://twitter.com/openviewventure" rel="noopener noreferrer" target="_blank">OpenView on Twitter</a><a href="https://www.instagram.com/openviewventure/" rel="noopener noreferrer" target="_blank">OpenView on Instagram</a><a href="https://www.facebook.com/OpenViewVenture/" rel="noopener noreferrer" target="_blank">OpenView on Facebook</a>

I just transitioned from the Chief Megaphone Operator to Advisor of 1Password. At 1Password I was part of the c-suite that raised $920M from top-notch VC-firms, executives, and artists for a valuation of $6.7B; was recognized as one of the top 100 Private Cloud companies by Forbes; exceeded 100,000 B2B customers (and many more individuals and families) with triple digit revenues and high double-digit revenue growth; launched the first 1P commercial (search "cybersecurity skincare"); and built out the marketing organization from the ground up. 

Raj Sarkar

CMO, Advisor | Google, Atlassian Alum

Raj says that most of the PLG advice out there today is missing a key foundational point: data. Many PLG companies still rely on traditional sales & marketing software that keeps data in silos. The key to winning in PLG starts with your data infrastructure, and wiring it up early helps you scale later.


Raj Sarkar (ex-1Password, Atlassian): PLG Data Infrastructure

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It takes 3 ingredients to build a software startup in today’s wild market: people, product and growth. Easier said than done. BUILD is here to help by featuring conversations between venture capitalist Blake Bartlett and the smartest folks in software. OpenView is a VC firm that invests in amazing companies like Datadog, Expensify and Calendly. Visit ov.vc for more details.

Alex MacCaw is the founder of Clearbit and Reflect, and his journey with each company has been wildly different. Clearbit took more of a “classic” startup approach and now he’s building his new company Reflect in with a totally different way—building a fully remote &amp; asynchronous “lifestyle” company that decidedly eschews VC money and the other common hallmarks of a tech startup.&nbsp;Alex shares everything he’s learned as a founder and why he believes building startups should not be one-size-fits-all.

Setting the Tone as a New CEO

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