Steve King is a five-time CEO with many exits to boot and now sits on the boards of exciting companies. With more than 25 years of leadership experience in the information technology sector, he has demonstrated a wealth of experience and complementary strengths, notably his proven expertise in Sales, Marketing, and Financial Leadership, and ability to execute in highly competitive environments. Before joining DocuSign, King led venture-backed Virtela and ZANTAZ as president and CEO.
Key Takeaways
(00:00–13:53) Joining E*TRADE During the Dot-Com Bubble
(13:53–23:00) Changing Playbook and Market Strategies
(23:00–31:38) The Strategy of Acquisition and Growth
(31:38-38:08) Importance of Strategy and Great People
(38:08–49:44) Customer Focus and Building a Team
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Building Category Leaders
Steve King, a five-time CEO and early pioneer in cloud technology, shares hard-earned insights from leading transformative companies like Zantaz and DocuSign. From navigating the dot-com bubble at E*TRADE to scaling email archiving before SaaS was mainstream, King reveals how conviction, strategic flexibility, and relentless customer focus shaped market-defining outcomes. This conversation covers leadership in high-growth environments, the realities of startup execution, and the mindset required to outmaneuver larger incumbents, while always staying grounded in evidence and team alignment.
1. Joining E*TRADE During the Dot-Com Bubble
Steve King, a five-time CEO and former head of DocuSign, shares his journey from Silicon Valley’s early digital content days to building some of the first successful cloud businesses. He began by converting paper-based content into digital formats, joining major players like Ziff Davis and later E*TRADE—where his accidental promotion to CEO of eOffering set him on a path of leadership in technology-driven financial services. He later joined Zantaz, where he helped build one of the earliest scalable cloud platforms for email archiving, anticipating regulatory needs before SaaS was widely understood. With strategic focus, a committed team, and customers like Citigroup, Zantaz turned early chaos into a multi-hundred-million-dollar exit and cloud pioneer status.
King attributes Zantaz’s success to three things: a management team with conviction, early access to high-level decision-makers in financial services, and relentless focus on scalability at a time when cloud infrastructure had to be built from scratch. His team’s ability to anticipate legal and compliance market shifts helped them expand into adjacent sectors like e-discovery. Later, with DocuSign, King saw a similar opportunity—taking a nascent technology and scaling it through both top-down enterprise sales and bottom-up adoption models. His approach combined product innovation with go-to-market experimentation, setting the stage for DocuSign’s rise to category leadership.
We only had a handful of customers, but the largest financial services firm in the world at the time was our customer. We had optimized our platform to scale to that level. We became one of the only games in town with a purpose-built platform for high-volume email archiving where you could actually retrieve the emails in the case of a regulatory investigation or a discovery request.
— Steve King
2. Changing Playbook and Market Strategies
Steve King explained that his experience at ETRADE and Zantaz influenced his decision to join DocuSign. At ETRADE, he advocated for the legalization of electronic signatures, which helped inspire the Federal E-Sign Act. When evaluating DocuSign in 2009, he noticed that early competitors were building clunky on-premise systems, while DocuSign was ahead with a cloud-based solution. He saw parallels with Zantaz, where a market with little initial analyst attention later grew into a multi-billion-dollar space. Convinced by DocuSign’s technical edge and potential, King accepted the CEO role.
Once in the role, King assessed the go-to-market strategy and shifted focus from large enterprise clients to the more promising mid-market segment, based on data showing lower friction and acquisition costs. This strategy included partnerships with the National Association of Realtors and Salesforce, using real estate as a beachhead market. Although there was early traction in enterprise, King prioritized the mid-market to build scale and product strength. He also addressed M&A considerations, specifically reflecting on a pitch to acquire EchoSign, and emphasized that acquisition decisions require careful evaluation of long-term strategic value.
We had a CMO who really took the lead in developing a strategy, working with our board members, and other outside resources that we could tap. And so we just didn't, “Hey, wake up one day, this sounds like a good idea, let's go do this.” We put work into it, we let the data drive our decision-making.
— Steve King
3. The Strategy of Acquisition and Growth
Steve King explained his M&A experience from Zantaz and E*TRADE, emphasizing that while acquisitions can be a useful growth tool, they must meet strict criteria—clear synergies, product or market expansion, and justified cost. He described how DocuSign evaluated acquiring EchoSign but ultimately decided against it due to a lack of compelling strategic value and the risk of giving up too much equity. The company believed it had a better product, a larger customer base, and the ability to outcompete larger incumbents without needing to buy a rival. The choice was controversial internally, but their conviction proved right as DocuSign eventually captured dominant market share.
King also noted that while DocuSign temporarily pulled back from the enterprise segment to focus on the mid-market, the long-term strategy was always to dominate the enterprise. He followed a proven SaaS playbook—starting bottom-up with individuals and departments before scaling to enterprise-wide deals, similar to Salesforce. In his current role mentoring startups, he encourages experimentation to find product-market fit, stressing the importance of identifying beachhead markets. Rather than rigidly sticking to a model, King advocates for pattern recognition, flexibility, and learning from market signals to guide early-stage companies toward scalable growth.
I believe that if you're gonna sell into enterprise, sell in B2B, you need to have a plan, a strategy for how you're gonna outmaneuver the large incumbents. Especially in the beginning, while you're establishing your market presence.
— Steve King
4. Importance of Strategy and Great People
Steve King emphasizes that successful company building starts with a clear, long-term vision—typically a three-year goal—and a disciplined process for breaking it down into yearly, quarterly, monthly, and daily actions. He avoids rigid “strategic planning” in favor of a flexible approach he calls “strategy as a process.” The idea is to align the team around a shared objective, then revisit and adjust the plan every six months based on what’s been learned and how the market has shifted. This method provides both structure and agility, making it easier to pivot, when necessary, without losing momentum or clarity.
Where companies succeed, according to King, is in their ability to stay aligned, make evidence-based adjustments, and maintain a forward-looking mindset. Failure often comes from clinging to old assumptions or being too slow to respond to new information. His approach applies beyond startups—it’s a mindset of continuous reassessment and improvement. Whether building a new product, launching a campaign, or running a business unit, success hinges on committing to a vision, staying adaptable, and being willing to evolve the strategy as reality unfolds.
For me, it starts with thinking. I'm reluctant to use strategy or strategic planning, especially for startups, but you do have to think through it. Where do you want to go? Where do you want to be in three years? Market factors are beyond your control, but you assume that you know the markets are stable. Where do you see yourself in your company in three years?
— Steve King
5. Customer Focus and Building a Team
Steve King underscores that building anything meaningful starts with assembling a team of exceptional, complementary people who believe in the vision as strongly as the founder. He points out that success comes not from assuming what the market needs, but from engaging deeply with customers, prospects, and industry experts, and using that input to refine the product over time. That was key in his decisions to invest in RELAYTO twice—he saw a founder constantly learning from the market and evolving the product based on real-world feedback, not just internal assumptions.
He warns against falling in love with your own ideas to the point where you ignore inconvenient truths. Smart leaders fail when they avoid feedback or get too emotionally attached to their original vision. The discipline to face reality, especially when it’s uncomfortable, and adjust course is what separates resilient companies from failed ones. King’s advice to younger leaders is grounded in his early sales experience: stay even-keeled, stay informed, and stay in the fight. You don’t get better by sitting on the sidelines—you improve by facing the hard facts head-on and using them to keep building.
I invested in RELAYTO because you were a force of nature, and you weren't going to let the inevitable obstacles and big walls that you're going to run into get in your way. You're going to find a way around them, and that's exactly what's happened. If you're going to build something great, you need a great team to help you do it.
— Steve King
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