1Password began as a practical solution created by two families—Dave and Sarah Teare, along with Roustem and Natalia Karimov—approximately 18 years ago. The tool was initially designed to help them test e-commerce sites more efficiently by automating the process of filling in login credentials, credit card information, and addresses.

What started as a "one-month project" to solve their own business needs quickly evolved when they realized its personal value. They enhanced the tool with additional security features and made it available as shareware. To their surprise, it gained significant traction, prompting them to focus exclusively on developing 1Password.

"I was Dave's boss back when we both worked at IBM... they had started 1Password really for themselves. They were building e-commerce sites at the time and needed a way to test them faster."

Timestamp: [00:00-03:32]

By 2011, 1Password had grown to a 20-person company—larger than the founders had envisioned or felt equipped to scale further. Facing a pivotal decision, they chose to bring in external leadership to guide the company's expansion rather than maintaining its small size.

They approached Jeff Shiner, a family friend of the Teares for over 25 years, to lead 1Password as CEO. When Jeff joined, his initial growth strategy was refreshingly straightforward: double the size of the company by essentially duplicating the excellent talent they already had.

"I remember back then saying 'I'm going to double the size of the company.' It was always like 'Why double?' Well, I can look at any individual who's there and say 'Man, they're doing a great job, I wish we had two of them.' I don't really know what I would do if it's like 'Yeah, we had 10 of them.'"

Under Jeff's leadership, 1Password began to broaden its horizon by internationalizing the product, making it accessible to users worldwide regardless of language or platform preferences.

Timestamp: [03:32-04:32]

1Password's growth strategy under Jeff Shiner centered on a fundamental philosophy: "Build a good product and support the heck out of your customers." This approach meant genuinely listening to customer feedback and responding to their needs.

During this phase, customers were increasingly requesting platform diversification. Windows users wanted a native application, Android users needed a full-featured app rather than just a "reader," and multi-platform users required seamless experiences across their various devices.

The company dedicated several years to addressing these needs, building out a comprehensive ecosystem of applications that worked harmoniously across different operating systems and devices, all while maintaining the intuitive user experience that had made 1Password popular.

Timestamp: [04:32-05:32]

Around 2013-2014, Jeff noticed a significant shift in how businesses were approaching 1Password. Initially, companies were purchasing 1Password licenses as Christmas gifts for employees, but this gradually evolved into a security-driven business decision.

"They started to shift and say 'Oh maybe we'll buy a copy of 1Password for all our employees to keep our business safe.' And that was the big shift in my mind. I'm like, we're going B2B now."

This pivotal moment forced 1Password to reconsider its entire product architecture. While the end-user experience remained largely consistent whether logging into personal or work accounts, the business version required entirely new capabilities including team management, organizational provisioning, deprovisioning, reporting, and auditing features.

Additionally, 1Password needed to transform from a traditional desktop application that synced through services like Dropbox or iCloud into a SaaS platform—a fundamental architectural change that presented significant challenges.

Timestamp: [05:32-06:58]

Despite the ambitious evolution to B2B and SaaS, 1Password approached these challenges with what Jeff calls "ignorance and hubris"—a philosophy borrowed from Don Melton, a founder of WebKit:

"How do you accomplish something amazing? You need two things: ignorance and hubris. Because if you know the problems that you're going to face, you'll never start it. And you just need to believe that you can do it."

Through this mindset, the company successfully built both the SaaS infrastructure and B2B capabilities, launching "1Password for Business" in 2016. While Jeff jokingly refers to this initial version as "1Password for bowling leagues," it represented their first step toward serving enterprise customers.

Throughout this entire journey, 1Password maintained profitability without external funding. The company embraced a bootstrapped approach, focusing on genuine customer relationships and building products that people would actually pay for rather than just express interest in.

"There's a difference between a user and a customer. If I go to my friends, my neighbors, whomever I meet and say 'Here's my idea, do you think it's great?' What are they going to say? 'Yeah, great idea!' If you go to them and try to sell it to them, you may get a very different reaction."

Timestamp: [06:58-08:03]

By 2018-2019, 1Password had grown to approximately 150 employees with 20,000-30,000 business customers. Despite this success, the company still lacked established sales, marketing, finance, and HR departments, operating with a relatively immature business infrastructure.

Jeff recognized that the company's extreme privacy and bootstrapped status—while previously a source of pride—was becoming a limitation. The lack of public information about the company's growth and financial stability made it difficult to attract the world-class talent needed to build sophisticated business functions.

"I want world-class marketing, I want world-class go-to-market... but how do I gain that? Well, you get world-class leaders to grow those orgs. How do you attract world-class leaders when a company like ours is so private? Nobody knew if we had money or if we were growing because we had never been public, we'd never raised money."

This realization led to 1Password's decision to pursue venture capital funding, not for day-to-day operations but to provide validation, "courage capital" for potential acquisitions, and to signal to the market that they were a serious, well-funded enterprise.

The resulting funding round with Accel became the largest Series A in Accel's history at that time, providing the company with both the capital and credibility to attract elite talent and accelerate their growth trajectory.

Timestamp: [08:03-10:20]

• 1Password began as a utility for testing e-commerce sites before evolving into a personal security tool and eventually an enterprise solution
• The company maintained profitability from day one, bootstrapping for 14 years before raising venture capital
• Their product evolution was guided by genuine customer feedback, following the philosophy "build a good product and support the heck out of your customers"
• The transition from consumer app to B2B platform required fundamental architectural changes, including building a SaaS infrastructure
• While 1Password didn't need venture capital for operations, they pursued funding to gain market validation and attract world-class talent
• The company's growth philosophy emphasized doubling in size strategically rather than explosive, unfocused scaling
• Jeff's approach to building featured "ignorance and hubris" - not knowing the full extent of challenges ahead but believing they could overcome them

Timestamp: [00:00-10:20]

People:

• Jeff Shiner - CEO of 1Password who joined when the company was at 20 employees
• Dave and Sarah Teare - Co-founders of 1Password, family friends of Jeff Shiner
• Roustem and Natalia Karimov - Co-founders of 1Password
• Don Melton - Founder of WebKit, quoted on accomplishing amazing things with "ignorance and hubris"
• Arun Matthew - Excel partner interviewing Jeff
• David Fogno - Mentioned as a resource introduced by Accel, later hired as President and COO

Companies/Products:

• 1Password - Password management and identity security solution
• IBM - Previous employer of Jeff Shiner and Dave Teare
• Accel - Venture capital firm that led 1Password's Series A funding round
• Dropbox/iCloud - Services initially used for syncing 1Password data before the SaaS transition

Concepts:

• Bootstrapping - Building a company without external funding, which 1Password did for 14 years
• SaaS (Software as a Service) - Business model 1Password transitioned to from traditional software
• B2B (Business-to-Business) - Market segment 1Password strategically expanded into
• "Courage Capital" - Term for raising money not for operations but for potential acquisitions and growth opportunities

Timestamp: [00:00-10:20]

Jeff Shiner's transition to CEO in 2011 presented unique challenges, particularly because he was taking over from founders who were also personal friends. This required careful navigation of personal and professional boundaries while establishing the necessary authority to lead effectively.

The initial leadership approach involved collaborative decision-making among the five key stakeholders—Jeff, Dave and Sarah Teare, and Roustem and Natalia Karimov. This structure allowed Jeff to gain understanding of the company before making significant changes.

"It's definitely very tricky, especially in a case like mine where Dave and Sarah were friends, because you have to navigate that line of 'I need control if I'm going to really take over,' but you don't want to upset either the founders or your friend."

Over time, as the company grew beyond its initial 20-person size, the leadership structure naturally evolved. The need for more formalized decision-making processes and hierarchies became evident, with more responsibilities gradually shifting to Jeff as CEO.

Timestamp: [10:24-12:27]

As 1Password expanded, the role of the founders had to evolve significantly. While founders naturally want to maintain influence and provide input on company direction, their interventions can have outsized impact that isn't always constructive as the organization scales.

When a company is small, founders' involvement is easily contextualized—employees understand their deep connection to the product and their long-term commitment. However, as the company grows and adds employees who don't have that historical context, founder interventions can create confusion and disruption.

"It often comes across as 'Oh my goodness, a founder came in and yelled at us,' and then chaos ensues. And that's where it starts to become difficult... as the company really starts to grow and it's more of a heartbeat of 'they're out now they're in, they're out now they're in.'"

This "in-and-out" pattern of founder involvement requires careful management and clear communication channels to ensure their valuable insights enhance rather than disrupt the company's operations.

Timestamp: [12:27-13:47]

1Password's growth journey can be organized into distinct phases: the bootstrapped founding by two couples, Jeff's arrival and initial scaling, and the venture capital-fueled expansion following their Series A with Accel.

A fundamental reality of scaling is that "everything changes every year, year and a half." Each doubling of company size introduces new organizational challenges that require adaptations in communication and structure.

"I remember even at the time we used to get everybody together in a circle and talk to them. And I remember at one point we got too big for the room, and so people—instead of a circle—sat themselves around the edges, and we called it a 'squircle.' And then eventually you get too big for even that room."

In the five years following their Series A investment, 1Password achieved exactly what they had hoped—attracting world-class talent to build out their executive team, including a CFO and CRO, while growing from 176 employees at the end of 2019 to more than 1,200 today.

This growth brought increased capabilities and maturity, though Jeff notes it hasn't necessarily made things easier: "There's always a challenge, there's always the next thing."

Timestamp: [13:47-15:16]

The way people work—and consequently, the security challenges companies face—has transformed dramatically over the past 15 years. Jeff reflects on his early career at IBM when security was more straightforward: physical presence in the office, company-issued hardware, and controlled software environments.

"15-odd years ago when I worked at IBM, I had my lanyard, I'd walk into the lab, I would badge in, I would sit at my desk where my computer was... It wasn't security issues around 'Is it actually me?' Of course it was me—I was there, I was present, I was working on machines they knew and software they knew."

Several developments have radically changed this landscape: the rise of SaaS applications, the proliferation of mobile devices implementing Bring Your Own Device (BYOD) policies, and most dramatically, the COVID-19 pandemic forcing widespread remote work.

During the pandemic's initial phase, companies prioritized operational continuity over security—focusing on enabling remote productivity with the intention to "catch up" on security later. In 2023, many organizations attempted to address these security gaps by requiring employees to return to offices, but this approach largely failed.

Timestamp: [15:16-17:52]

By 2024, companies have largely accepted that hybrid work environments are here to stay, creating permanent security challenges that traditional perimeter-based approaches can't solve. This reality has led many organizations to seek 1Password's help with securing their increasingly decentralized workforces.

"In 2024, companies are now like, 'Okay, this hybrid work environment is going to stay.' And over the last at least year, year and a half now, they've been reaching out to me saying, 'Help us!'"

While organizations have implemented managed environments with single sign-on (SSO) solutions like Okta and device management tools like Kolide, they struggle with the expanding perimeter of unmanaged devices and the proliferation of unauthorized SaaS applications entering their environment.

Unlike the enterprise software of the past, which went through lengthy procurement and implementation cycles, today's SaaS tools often enter organizations through individual employees: "My friend saw Notion, and I'm going to go and give Notion a try."

This shadow IT presents significant security risks that traditional approaches aren't equipped to handle, creating the opportunity that 1Password is now addressing.

Timestamp: [17:52-18:54]

In response to the evolving security landscape, 1Password has expanded beyond its origins as a password manager to develop what they call "Extended Access Management." This solution addresses the fundamental tension in cybersecurity between protection and productivity.

"It's easy to be secure at the expense of productivity. It's easy to be productive at the expense of security. It's very difficult to do both. And so we do both by offering what we call Extended Access Management."

Extended Access Management provides comprehensive security by protecting "every login for every app on every device regardless of where your employee is." This approach acknowledges the reality of modern work environments while maintaining security standards.

1Password unveiled this new solution at the RSA Conference approximately six weeks before this interview, receiving enthusiastic response from potential customers. While Jeff acknowledges that they still need to convert this interest into actual business, he's excited about the potential market for this expanded offering.

Timestamp: [18:54-19:55]

• Taking over from founders requires careful navigation of authority while maintaining relationships, especially when personal friendships are involved
• As companies scale, founders' roles must evolve from direct intervention to more structured influence to avoid creating organizational chaos
• Organizational structures and communication methods must continuously adapt as companies grow—what works at 20 people won't work at 200 or 2,000
• The modern security landscape has been transformed by SaaS applications, mobile devices, and hybrid work arrangements that render traditional perimeter-based security insufficient
• The COVID-19 pandemic accelerated the shift to remote work, creating security challenges as companies prioritized operational continuity
• The failed "return to office" attempts of 2023 forced companies to accept hybrid work as permanent, creating demand for new security approaches
• 1Password has evolved from a password manager to an "Extended Access Management" solution that balances security and productivity in hybrid environments
• Growing companies face continuous challenges regardless of size—scaling successfully requires constantly adapting to new circumstances

Timestamp: [10:24-19:55]

People:

• Jeff Shiner - CEO of 1Password who transitioned into the role in 2011
• Dave and Sarah Teare - Co-founders of 1Password who were friends with Jeff before hiring him
• Roustem and Natalia Karimov - Co-founders of 1Password
• Jeannie - First hire Jeff made as CFO after raising capital
• Julian - Second executive hire as CRO (Chief Revenue Officer)

Companies/Products:

• 1Password - Password management and identity security solution
• IBM - Jeff's previous employer, used as an example of traditional office-based work
• Okta - Single Sign-On (SSO) solution mentioned as part of managed enterprise environments
• Kolide - Device management solution mentioned alongside Okta
• Notion - Example of a SaaS application that might enter organizations through individual employees rather than formal IT processes
• SAP - Referenced as an example of traditional enterprise software with lengthy implementation processes

Concepts:

• Extended Access Management - 1Password's evolved security solution beyond password management
• BYOD (Bring Your Own Device) - Policy allowing employees to use personal devices for work
• Shadow IT - Unauthorized applications and services used within organizations
• SSO (Single Sign-On) - Authentication service that permits users to use one set of credentials across multiple applications
• MDM (Mobile Device Management) - Software for administering and securing mobile devices in an enterprise environment
• Squircle - Humorous term coined for when the company outgrew circle meetings and people sat around the edges of rooms

Events:

• RSA Conference - Security conference where 1Password launched their Extended Access Management solution approximately six weeks before this interview
• COVID-19 Pandemic - Transformative event that accelerated remote work adoption and created new security challenges

Timestamp: [10:24-19:55]

1Password has maintained cash flow positivity throughout its growth journey, allowing them to approach funding with a different mindset. Rather than requiring investment for day-to-day operations, they've used capital strategically to accelerate their roadmap.

Following their initial Series A with Accel, the company secured a smaller Series B round as Accel wanted to invest further, and then completed a substantial Series C round with additional investors. Across these three funding rounds, 1Password has raised a total of $920 million.

"Our appetite has grown, and so now when we look at that additional funding... that gives us a huge amount of courage capital for us to do the M&A, for us to look at it and say, 'Are there big opportunities, big bets that we can make to accelerate that roadmap?'"

This "courage capital" provides 1Password with the financial flexibility to pursue acquisitions and major strategic initiatives without compromising their operational independence or profitability.

Timestamp: [20:02-20:59]

1Password has a unique position in the security market, having started as a consumer product before expanding into B2B and enterprise solutions. This creates the challenge of balancing potentially competing customer segments with different needs and expectations.

When considering this balance, Jeff rejects the simplistic approach of abandoning the consumer business despite it representing a minority of their revenue. Instead, he recognizes the strategic value of maintaining a strong consumer presence.

"Let's look at it dramatically and say, 'Ah, forget that consumer business, we don't need them.' Well, if I'm going to not have a password manager at home... what am I going to do? I use 'fluffy cat' for all my stuff at home. Guess what habit I'm bringing into the office regardless of what tool they give me? We're using 'fluffy cat' in all of my things in the office."

This insight underscores a fundamental reality of security: user behavior at home affects security practices at work. By maintaining a strong consumer product, 1Password helps establish secure habits that transfer to the workplace, creating a more complete security solution.

Timestamp: [20:59-22:34]

1Password's strategy extends beyond the traditional separation of work and personal devices to address the reality of how people actually use technology. Jeff emphasizes the importance of having their solution available on all devices a person might use, regardless of whether they're company-issued or personal.

The modern work environment frequently involves people using personal devices for work purposes—like having Slack installed on a personal iPad kept beside their bed. By having 1Password available on these devices, users can maintain security across contexts by simply adding their business account to the app they already use for personal passwords.

"When they're working at the office with their company-issued computer, that's one thing. But then when they go home and it's that iPad that's beside their bed that maybe they mostly use for games—but maybe they've got Slack installed on it, Slack for work—if they have the 1Password app on there, they have all of their home stuff. They just simply add their business account, they can log into that and stay secure."

Rather than viewing their consumer business through a purely financial lens—attempting to maximize revenue from individual users—1Password sees it as part of a "flywheel effect" and a competitive moat that strengthens their overall security offering.

Timestamp: [22:34-23:31]

Instead of focusing on extracting maximum revenue from consumers, 1Password has implemented an innovative approach that aligns business and consumer interests while expanding their user base: providing free family accounts to employees of business customers.

"For a business account, if you have a business account, every employee at that business gets a free family account. It's completely separate from the business account, but it's a way we can give it to them for free."

This strategy creates multiple benefits:

1. It encourages secure password practices across all aspects of an employee's digital life
2. It exposes 1Password to the employee's family members, who may work at other companies
3. It builds loyalty and positive sentiment toward the product
4. It creates a natural growth vector when employees change jobs

This approach demonstrates how 1Password balances different customer segments by clearly defining the value each provides to the overall business strategy, rather than treating all segments as needing to contribute equally to revenue.

Timestamp: [23:31-24:13]

Arun observes that 1Password's approach differs from most competitors by taking a holistic, human-centric view of security. Rather than separating work and personal security as distinct domains, they focus on protecting the person across all contexts of their digital life.

"You take a very holistic view of your customer in that it's not just protecting their work applications or devices, it's not just protecting their home, but it's protecting the person... That human-centric approach that you have, I think, is partly what defines you and differentiates you in the market."

This philosophy has guided 1Password's emphasis on user interface and experience design, making their product accessible even to less technically savvy users. As Arun notes, this approach creates a virtuous cycle: by designing for the least technical consumer, they create a product that's easier to adopt and use in enterprise contexts as well.

Jeff agrees with this assessment, attributing their success to consistently listening to customers and understanding that security solutions must provide value to the end-user, not just to the business purchasing the software.

Timestamp: [24:13-25:17]

A key insight driving 1Password's product philosophy is the recognition that traditional security applications often provide little value to end-users while adding significant friction to their experience.

"In general, security apps don't give much to the end user. If anything, they add friction. You look at things like CAPTCHA—how annoying is CAPTCHA, right? 'Please click on all of the buses,' and they've got one bus across the whole nine things, and you're like, 'Is this little corner of the bus in this square?'"

1Password recognized from its origins as a consumer application that successful adoption requires giving users tangible benefits, not just imposing security requirements. This means providing value to the individual using the product, not just to the business purchasing it.

Jeff emphasizes that companies often forget that employees are people first—they don't transform into different entities at work versus at home. Security solutions that acknowledge this reality and provide consistent value across contexts are more likely to succeed.

"We'll talk about B2C and B2B as if they're—like, am I 'work Jeff' or am I 'home Jeff'? No, I'm Jeff. It's a weird thing. So I do think we have to look at that, but you have to look at it and say, 'What am I giving the person who's using my app, not the person that I'm selling my app to?'"

Timestamp: [25:17-26:48]

When asked what advice he would give his past self from five years ago regarding funding decisions, Jeff offers two key insights:

First, he acknowledges that 1Password waited too long to seek external investment. While bootstrapping for 14 years became a source of pride, it ultimately delayed the company's growth trajectory.

"I took funding too late. Again, we'll tell people, 'Oh, we've been bootstrapped for 14 years,' and they'll congratulate us on that. And it became almost a source of pride, and you don't realize there's a ton of value if you take the funding and you have a purpose for it."

Second, he emphasizes that entrepreneurs must always have a purpose for funding that extends beyond the money itself. This means selecting investors based on the value they bring to the relationship, not just the size of the check they offer.

"Are you picking a person and a VC because they're offering you the biggest amount? Big mistake. You need to look at what you're going to get from them that's above and beyond the funding, because that's the value that's going to either add nothing or add a ton."

Timestamp: [26:48-28:15]

When seeking investors, 1Password looked beyond capital to find partners who could provide strategic value based on relevant experience. For their initial funding with Accel, Jeff was attracted by the firm's experience with companies following similar trajectories, particularly Atlassian.

"One of the things that really attracted me to Accel was things like Atlassian. The fact that Atlassian... followed a similar path to us. And you were able to show us that you were able to—I was able to talk to them and say, 'What was that? What was the value? What would they have done differently?'"

For their Series C round, 1Password brought in celebrity investors like Ryan Reynolds, Robert Downey Jr., Trevor Noah, and Mary Barra, recognizing the marketing value these associations provided. Jeff frames this decision in practical terms:

"What would it cost for me to pay Robert Downey Jr. and Ryan Reynolds and Trevor Noah and Mary Barra and all of these others to even mention 1Password? Here they're giving me money to be part of the round."

This approach demonstrates how 1Password consistently views funding decisions through the lens of strategic value beyond the capital itself, whether that's industry expertise, relevant connections, or marketing opportunities.

Timestamp: [28:15-29:15]

• 1Password has raised $920 million across three funding rounds while maintaining positive cash flow, using capital for strategic acceleration rather than operations
• The company maintains its consumer business despite it representing a minority of revenue, recognizing that home security habits directly impact workplace security
• Their cross-device strategy acknowledges the reality of modern work, where personal devices are often used for work applications
• The free family account offering for business customers creates a growth flywheel and strengthens security across contexts
• 1Password's human-centric approach focuses on protecting people rather than just devices or applications, differentiating them in the market
• Traditional security solutions often add friction without providing value to end-users, while 1Password prioritizes user benefits
• Jeff advises entrepreneurs not to wait too long for funding and to select investors based on strategic value beyond capital
• Celebrity investors in their Series C round were chosen primarily for their marketing value rather than just their financial contribution

Timestamp: [20:02-29:15]

People:

• Jeff Shiner - CEO of 1Password
• Arun Mathew - Partner at Accel interviewing Jeff
• Mike and Scott - Presumably Atlassian founders Mike Cannon-Brookes and Scott Farquhar, who Jeff spoke with about their experience
• Ryan Reynolds - Celebrity investor in 1Password's Series C round
• Robert Downey Jr. - Celebrity investor in 1Password's Series C round
• Trevor Noah - Celebrity investor in 1Password's Series C round
• Mary Barra - Celebrity investor in 1Password's Series C round (CEO of General Motors)

Companies/Products:

• 1Password - Password management and identity security solution
• Accel - Venture capital firm that led 1Password's Series A funding round
• Atlassian - Company Jeff mentioned as following a similar trajectory to 1Password, also backed by Accel
• Slack - Communication platform used as an example of work applications that might be installed on personal devices

Concepts:

• Courage Capital - Term for raising money not for operations but for potential acquisitions and growth opportunities
• Flywheel Effect - Self-reinforcing growth mechanism where each new user increases the value of the product
• B2B (Business-to-Business) - Market segment where 1Password sells to organizations
• B2C (Business-to-Consumer) - Market segment where 1Password sells directly to individuals
• CAPTCHA - Security measure that adds friction to user experiences, used as an example of problematic security interfaces
• Human-Centric Security - Approach that focuses on protecting individuals across all contexts rather than just specific devices or environments
• Free Family Account Strategy - 1Password's approach of providing free family accounts to employees of business customers

Timestamp: [20:02-29:15]

1Password has operated as a remote-first company since its inception, long before the COVID-19 pandemic made this approach commonplace. This experience has given them valuable insights into effectively managing a distributed workforce, which Jeff readily shares while acknowledging they "don't do any of this perfectly."

The cornerstone of successful remote work, according to Jeff, is communication. In 1Password's earlier days when they had around 100 employees, they would bring the entire company together on annual cruises to build connections. As they've grown to more than 1,200 employees, they've adapted to more team-based gatherings, like the customer experience team meeting in New York during this interview.

"Communication is key, and what we try to do is find ways we can make it very clear to everybody in the company what the purpose is."

To maintain alignment across a large, distributed organization, 1Password focuses on clearly articulating company themes—four key priorities that guide their work through the end of 2024. These themes are consistently repeated and emphasized to ensure everyone understands the company's direction and purpose.

Jeff emphasizes that without this clear, consistent communication, organizations risk gradual misalignment: "People have a general understanding of what we're doing, but they're all off just sort of flying two degrees away from each other... if you're flying off two degrees and you have 1,200 people, and every month that's another two degrees, 90 degrees happens pretty quickly."

Timestamp: [29:19-32:03]

When discussing AI applications at 1Password, Jeff frames the company's approach through his philosophy of "giving meaning to data." While their Watchtower feature (which identifies weak or reused passwords) doesn't use AI, it exemplifies how 1Password adds value by making password data more meaningful to users.

Jeff sees significant potential for AI to enhance this capability without compromising privacy or security, particularly by building models that operate locally. He cites an existing example: an ML model implemented years ago that helps the 1Password extension recognize whether a webpage is for sign-in or sign-up, allowing appropriate autofill behavior despite the lack of standardization across websites.

"We have an ML model... that we train to understand what a web page looks like. So when you go to a web page with the 1Password extension, it will say, 'Oh, is this a sign-up page or a sign-in page?' Because if you're signing up for something, we're going to give the email address and recommend a password. If you're signing in, we're going to do an email and your password."

This existing functionality demonstrates 1Password's pragmatic approach to machine learning for improving user experience without compromising their core security values.

Timestamp: [32:03-33:53]

When asked about monetizing AI features, Jeff takes a notably pragmatic stance. Rather than viewing AI as a distinct product category to charge for separately, he sees it as a fundamental enabler of business capabilities that will soon be table stakes.

"I often get asked, 'What keeps me up at night?' And it's like, 'Which competitor is this?' I always say the same thing... what keeps me up at night is, 'Can we move at the speed of technology?' So before I worry about can AI add yet another level of revenue generation, you have to look at it from a standpoint of: if I'm not using AI, I'm going to just lose."

Jeff believes AI will be transformative enough that companies failing to leverage it effectively will struggle to survive, making the question of additional revenue secondary to the existential need to incorporate AI capabilities.

When considering AI monetization, Jeff envisions it fitting into a "good, better, best" tiered pricing model where AI-enhanced capabilities might encourage customers to upgrade to premium tiers. However, he doesn't foresee selling "AI bundle one" as a standalone offering.

Instead, he sees AI as enabling valuable business capabilities—like intelligently analyzing shadow IT to identify security risks—that customers would be willing to pay for because of the business value they deliver, not because they use AI specifically.

Timestamp: [33:53-36:22]

1Password's journey from 170 employees after 14 years to more than 1,200 in just five additional years provided Jeff with valuable insights about selecting leadership for different company stages. He distills his approach into two key principles: "attitude and aptitude matter."

"People sometimes talk about 'our company has a culture.' No, your company's culture is going to be defined by the people in your company, and in particular by the leadership of your company."

Leaders significantly influence company culture, so hiring someone whose approach and values aren't aligned with the organization can have detrimental effects—either changing the culture negatively or creating conflict. This makes cultural fit essential when evaluating executive candidates, regardless of their technical capabilities.

The second principle involves matching a leader's experience to the company's current stage. It's not enough for candidates to express interest in working at a company of a particular size; their recent experience should be relevant to the specific challenges of that stage.

"If you're looking at, say, a Chief Marketing Officer of a company, and you're 150 people or 500 people, you still need that person to be down in the weeds and actively growing your marketing org. So even if they've done that seven, eight years ago and are interested in doing it again, are they close enough, have they stayed close enough to where they understand how to do that in 2024?"

Timestamp: [36:22-39:04]

Despite being a remote-first company, Jeff emphasizes the importance of regular in-person gatherings for the executive team. With eight executives distributed across various locations—California, Seattle, Montreal, Toronto, and Washington DC—they prioritize meeting in person every six to eight weeks.

"Humans are still humans and want to talk."

This simple statement reflects 1Password's pragmatic approach to remote work—leveraging the advantages of distributed teams while acknowledging the fundamental human need for face-to-face interaction, particularly among leadership teams making critical decisions.

Timestamp: [39:04-39:26]

When asked what excites him about 1Password's future and the security industry, Jeff focuses on the company's potential to make a meaningful difference rather than chasing industry trends. While acknowledging the excitement around new challenges like AI security, he emphasizes that many of the most serious security problems are "decades old"—particularly those involving human behavior.

"The vast majority of actual threats to a company are things like people, and that's what we're here to help. We're here to help people."

Jeff's vision for 1Password centers on growth not merely as a business objective but as a means to increase their positive impact. He articulates this vision through a memorable phrase:

"We have to hit above our weight, and we have to weigh more. We have to be more impactful. And as we continue to grow as a company, that gets easier and easier, to have a broader scope with which we can impact in a positive way."

This combination of high ambition and human-centered purpose reflects the values that have guided 1Password from its origins as a small bootstrapped company to its current position as a security leader with more than 1,200 employees.

Timestamp: [39:26-40:46]

• Effective remote work depends on crystal-clear communication about company purpose and priorities
• Without consistent alignment, distributed teams can gradually drift off course, with even small deviations compounding over time
• 1Password approaches AI as a means to "give meaning to data" rather than as a standalone feature set
• The company already uses machine learning to improve user experiences, like intelligently identifying webpage types for appropriate autofill behavior
• Jeff views AI implementation as a business necessity rather than an optional revenue stream—companies that fail to leverage AI effectively risk becoming obsolete
• Leadership selection profoundly influences company culture, making attitude and values as important as technical capabilities
• Executive candidates must have recent, relevant experience for the company's current stage, not just past experience with similar-sized organizations
• Even in remote-first companies, regular in-person meetings remain essential for executive teams
• Many of today's most significant security threats involve human behavior rather than new technologies
• 1Password's mission is to grow not just as a business but in its capacity to positively impact security challenges

Timestamp: [29:19-40:46]

People:

• Jeff Shiner - CEO of 1Password
• Arun Mathew - Partner at Accel interviewing Jeff

Companies/Products:

• 1Password - Password management and identity security solution
• Watchtower - 1Password feature that identifies weak or reused passwords

Concepts:

• Remote-First Work - Organizational structure where distributed work is the default rather than an accommodation
• Extended Access Management - 1Password's expanded security offering beyond password management
• Shadow IT - Unauthorized applications and services used within organizations
• Good, Better, Best Pricing - Tiered pricing strategy that Jeff envisions for incorporating AI capabilities
• Machine Learning - Technology already used by 1Password to improve webpage detection for autofill
• Company Themes - 1Password's approach to maintaining organizational alignment through four key priorities

Locations:

• New York - Location of the customer experience team offsite mentioned in the interview
• California - Home to two 1Password executives
• Seattle - Home to one 1Password executive
• Montreal - Home to two 1Password executives
• Toronto - Home to two 1Password executives (including Jeff)
• Washington DC - Home to one 1Password executive

Timestamp: [29:19-40:46]