Outreach Executive and Leadership Team

August, 2026

Leadership Overview

Outreach has 4 executives leading key functions including marketing, revenue operations, corporate strategy, and organizational mission.

Focused on transforming sales execution, Outreach empowers market-facing teams to create and close pipeline through advanced automation and artificial intelligence, ensuring maximum efficiency across the entire revenue cycle.

Leadership Roles at Outreach

  • President - Albert Sananes
  • Missionary President - Ruby Bostic
  • Chief Marketing Officer - Holly Simmons
  • Chief of Staff, Office of the CRO - Caitlin Crawford
  • Albert Sananes - President

    Albert Sananes, the President at Outreach, oversees the company's overarching business strategy and operational execution. Sananes directs the integration of artificial intelligence and automation across the sales execution platform to ensure market-facing teams achieve peak performance. By managing the company's growth trajectory, the President ensures that prospecting, deal management, and forecasting tools remain at the forefront of the industry. This leadership role involves coordinating with the Board and executive team to scale operations across global markets. Albert Sananes drives the organizational vision, focusing on the long-term impact of the platform on revenue cycle efficiency. Through strategic oversight of all go-to-market activities, the President maintains a focus on delivering measurable value to customers. By fostering a culture of innovation and operational rigor, Sananes secures the company's position as the leading provider of sales execution technology, consistently driving revenue growth and market expansion.
    Albert Sananes

    Ruby Bostic - Missionary President

    Ruby Bostic, the Missionary President at Outreach, leads initiatives focused on organizational culture and the core mission of the company. Bostic architects programs that align personnel with the fundamental goal of helping revenue leaders succeed through advanced sales execution technology. By overseeing internal engagement and mission-driven activities, the Missionary President ensures that the company's values remain central to all go-to-market operations. This leadership role involves cultivating a unified workforce dedicated to the platform's success in the competitive CRM software space. Ruby Bostic drives the development of internal training and development frameworks that enhance the effectiveness of teams across the revenue cycle. Through consistent focus on the company's purpose, the Missionary President supports the broader strategic objectives of the executive team. By championing the organizational mission, Bostic ensures that every team member understands the impact of the platform on customer success and long-term business growth.

    Holly Simmons - Chief Marketing Officer

    Holly Simmons, the Chief Marketing Officer at Outreach, directs global brand strategy and demand generation initiatives. Simmons architects comprehensive marketing programs that amplify the platform's value proposition to revenue leaders worldwide. By overseeing lead acquisition and market positioning, the Chief Marketing Officer ensures alignment with the company's goal of increasing go-to-market effectiveness. This leadership role involves managing cross-functional campaigns that drive pipeline growth across North American and EMEA markets. Through data-driven insights, Holly Simmons optimizes the customer journey from initial prospecting to final deal management. The Chief Marketing Officer collaborates closely with product teams to refine messaging, ensuring the sales execution platform remains the industry standard. By scaling marketing operations, Simmons secures a competitive advantage, ultimately fostering sustainable revenue growth and strengthening the brand presence within the highly dynamic software CRM landscape.
    Holly Simmons

    Caitlin Crawford - Chief of Staff, Office of the CRO

    Caitlin Crawford, the Chief of Staff, Office of the CRO at Outreach, manages strategic operations and internal communications for the revenue organization. Crawford coordinates high-priority projects that enhance the efficiency of sales execution activities. By overseeing the alignment of revenue teams, the Chief of Staff, Office of the CRO ensures that forecasting and deal management processes function with precision. This leadership role involves facilitating communication between the Chief Revenue Officer and department heads to streamline go-to-market activities. Caitlin Crawford drives operational excellence by implementing standardized workflows that support predictable pipeline closure. Through rigorous analysis of revenue cycle performance, the Chief of Staff, Office of the CRO identifies opportunities for process improvement. By managing the executive agenda and cross-departmental initiatives, Crawford supports the broader mission of maximizing the effectiveness of all personnel involved in the revenue generation process.

    Explore Leadership Teams in Customer Engagement Platforms

    Frequently Asked Questions Regarding Outreach Top Executives and Leadership Team

    Who leads Outreach?
    Outreach is led by Albert Sananes (President), along with executives such as Ruby Bostic (Missionary President) and Holly Simmons (Chief Marketing Officer).
    Who is part of Outreach’s executive team?
    The executive team of Outreach includes leaders such as Albert Sananes (President), Ruby Bostic (Missionary President), Holly Simmons (Chief Marketing Officer) and other senior executives.
    How many executives does Outreach have?
    Outreach has 4 executives leading key business areas.
    What roles are included in Outreach’s leadership team?
    The leadership team of Outreach includes roles such as President, Missionary President, Chief Marketing Officer, Chief of Staff, Office of the CRO.