Unicorn Leaders – David Obrand, CEO, Salesloft

In the episode, David provided additional background on Salesloft, emphasising its AI-powered platform’s role in guiding customer-facing teams with insights for consistent actions throughout the customer journey, from initial contact to renewal, for their global customer base exceeding 6,000.

David recounted a pivotal moment in fall 2022 when he received a call from Kyle Porter and Steve Goldberg, Salesloft’s CRO at the time, inviting him for a drink in New York. During their conversation, Kyle expressed how Salesloft was consistently surpassing previous milestones and his personal commitment to step down after 10 years to support his wife’s endeavors. Sharing aligned values and visions, David found himself increasingly drawn to the opportunity over several months of discussions. His previous experience as a Salesloft customer also influenced his decision-making process.

David reflected on the transition into Salesloft, emphasising the importance of Kyle Porter, the founder, initiating the change rather than it being driven solely by investors. This approach ensured a smoother transition, particularly due to the company’s robust culture. He expressed gratitude towards Kyle for aligning their visions and values, which facilitated the integration process. David highlighted the ongoing connection with Kyle, who remains on the board, symbolising a transition from successor to a collaborative relationship, with Kyle now partially serving as his boss on the board.

David discussed the impact of Vista’s involvement in Salesloft in the winter of 2021, which set the company on a trajectory of growth. He outlined three key areas where the raised capital was allocated: innovation, customer success, and ecosystem development. The focus on innovation aimed to meet the evolving needs of enterprise clients across over 30 countries, necessitating both organic and inorganic growth strategies. Customer success initiatives focused on supporting clients through workflow platforms, guiding them through organisational changes to maximise outcomes. Lastly, investments in the ecosystem aimed to complement internal innovation efforts and enhance customer success by leveraging external partners and resources.

David indicated that Salesloft currently doesn’t have plans for further funding rounds due to their favorable financial position. He credited Kyle Porter’s approach of prioritising responsible and mature growth over rapid expansion at any cost. Vista’s investment further reinforced this strategy, emphasising growth while ensuring profitability. This approach grants Salesloft the flexibility to control its trajectory independently without the immediate need for additional capital.

David outlined Salesloft’s current organisational structure, noting a workforce of approximately a thousand employees headquartered in Atlanta with additional offices across the U.S., Guadalajara, London, and Poland. He highlighted the company’s adoption of a hybrid work model, acknowledging the diverse preferences among employees for in-office, hybrid, or fully remote work arrangements. Salesloft prioritises providing tools and resources to support employees in delivering exceptional work and serving customers effectively, regardless of their preferred work environment.

David expressed enthusiasm about Salesloft’s acquisition of Drift, a buyer experience and conversational AI company. He explained that Salesloft’s vision is to transform the sales profession comprehensively, which led to the realisation that addressing the buyer side of the equation was essential. Drift, renowned in the industry for its technology, had been a valuable partner to Salesloft for several years before the acquisition. By integrating Drift’s capabilities into Salesloft’s platform, they aimed to provide customers with insights and actions based on buyer signals, enabling them to respond effectively to evolving buyer behaviours. This acquisition expanded Salesloft’s vision to transform the sales process for both buyers and sellers, facilitating the achievement of repeatable outcomes.

Following the acquisition of Drift, David highlighted the alignment of their culture with Salesloft’s strong focus on customer centricity and shared values. The leadership teams from both companies collaborated to reassess Salesloft’s values, recognizing the opportune moment to redefine them as Salesloft entered a new phase of growth. Beyond values, they also examined how they wanted to embody these values daily, not only internally but also in interactions with prospects, customers, and partners. Utilising a bottom-up approach, Salesloft’s Senior Leadership Team (SLT) engaged in discussions and made recommendations, fostering seamless collaboration across the organisation. Within 45 days of announcing the acquisition, they successfully rolled out the evolved values to the combined organization, ensuring continuity and alignment moving forward.

David emphasized his active involvement in internal communications to ensure alignment and engagement across Salesloft’s distributed workforce. Recognising the challenges of remote work, especially in a hybrid environment, they prioritize hyper-communication through monthly newsletters, all-hands meetings, daily leadership team standups, and weekly deep-dive operating reviews. Monthly all-hands meetings serve as critical touchpoints for fostering connection and alignment among employees. Additionally, Salesloft has implemented a charter for the business, cascading from top leadership down to every employee, to ensure everyone feels connected to the company’s priorities. These efforts, combined with active Slack channels, contribute to Salesloft’s effective internal communication and employee engagement strategy.

David expressed scepticism about the continued relevance of the term “unicorn” in the current market landscape, pointing out  the potential dangers of focusing on valuations and funding rounds. He highlighted the importance of celebrating metrics like customer growth, retention, and expansion, rather than solely relying on investor validation. David noted the shifting market dynamics, where going public now requires significantly higher revenue thresholds compared to previous years. Consequently, he cautioned against placing undue emphasis on valuations as a primary measure of success in today’s market.

David highlighted the importance of embedding AI not only in the product but also in the organisation’s mindset and operations. He pointed out Salesloft’s strong foundation in AI, with over four years of integration into the platform. Their leadership team, including R&D, Product, and Engineering heads, has been instrumental in architecting the platform to leverage both native and off-the-shelf AI solutions effectively. David underscored the significance of flexibility in catering to diverse enterprise preferences, ensuring compatibility with existing tech stacks like IBM or Microsoft. Salesloft’s platform architecture allows seamless integration of various AI technologies, reflecting their commitment to evolving with the AI landscape while also building proprietary AI capabilities to address specific use cases.

David elaborated on Salesloft’s partnership with IBM Watson X, noting that IBM had been a customer since 2018, initially deploying Salesloft within its digital sales team. Following successful implementation, IBM expanded the usage across its digital sales division and is now in the process of rolling it out to over 40,000 users globally. Through this partnership, Salesloft gained insights into IBM’s approach to Watson and Watson X, identifying an opportunity to extend their offering to IBM’s global customer base. The partnership entails Salesloft distributing its technologies globally, with IBM’s sales team trained to utilise and promote them to customers, showcasing the capabilities of WatsonX.

David outlined Salesloft’s plans for the next 12 to 18 months, mentioning global expansion and operational growth. They recently established a European headquarters in London and are scaling operations in Poland and Guadalajara to better serve their global enterprise clientele. In the US, they’re investing in expanding their presence, particularly in the Northeast region with the acquisition of Drift providing a base in Boston. Innovation, customer success, and ecosystem development remain key investment priorities, with upcoming releases including a summer update and the launch of the next platform generation, Arc, in the fall. David also hinted at potential future acquisitions, aiming to strengthen Salesloft’s position and provide enhanced value to customers.