Head of Sales & Client Engagement

The Organization
At TWG Group Holdings, LLC (‘TWG Global'), we are at the cutting edge of innovation and business transformation, leveraging data and AI to manage a diverse portfolio that spans Investments, Securities, Insurance, Finance, Corporate Lending, Merchant Banking, as well as Sports, Media, and Entertainment. Data is one of our most valuable assets, and our commitment to AI allows us to transform that data into a powerful competitive advantage. We are pioneering a range of data and AI services that provide real-time intelligence to both our customers and workforce, enabling them to make informed decisions within interactive, cloud-native business applications.
As we evolve into an AI-first, model-driven, and cloud-native company, we prioritize responsible data and AI practices that protect our customers and workforce while ensuring compliance within a regulated environment. Our goal is to lead by example, acting with the highest standards of ethics, responsibility, and transparency. This commitment drives our development of cutting-edge AI/ML business applications across our diverse product and service offerings.
In this role, you will be at the heart of our data and analytics transformation, collaborating closely with management teams to achieve our strategic objectives and operational excellence. Our decentralized structure empowers each business unit to operate autonomously while benefiting from the strategic guidance and support of our central AI Solutions Group.
Through our pioneering partnerships with major data and AI vendors, you will have the opportunity to work on transformative projects that will revolutionize marketing, distribution, customer acquisition, and internal processes. These initiatives are designed to enhance productivity, reduce costs, and create high-demand products and services. The advanced data systems we develop will grant management unparalleled access to real-time performance data, enabling swift, informed decision-making and agile business adjustments.
Moreover, you will play a crucial role in leveraging our strategic relationships and equity positions in leading tech startups. These collaborations are not just about staying ahead of the competition—they are about creating true competitive advantages across our businesses. You will contribute to projects that are reshaping industries, from harnessing cloud-based supercomputing capabilities to driving key initiatives with major universities that are shaping the future of technology.
At TWG Global, your work will directly contribute to our ambitious goal of generating sustained growth and superior returns, with expected annual equity returns exceeding 20%, including growing dividends. Join us as we push the boundaries of technology and innovation, delivering significant value across our portfolio while making a profound impact on the industries we serve.
We're looking for a Head of Sales & Client Engagement to lead the charge on go-to-market. You'll be both a dealmaker and a builder—owning high-stakes sales cycles while laying the foundation for a repeatable, scalable sales motion. This is a chance to help define how AI solutions are sold at a moment when the market is being rewritten.
This role reports directly to the Head of AI Business Development and collaborates cross-functionally with product, engineering, and the broader TWG ecosystem.
If you thrive in fast-paced environments, love building from scratch, and are energized by selling complex solutions to sophisticated buyers, this role is for you.
Key Responsibilities:

• Build pipeline: Identify top targets, craft outreach strategies, and establish early traction with enterprise buyers
• Run your own qualification calls: Lead discovery conversations with prospective clients to deeply understand their pain points and evaluate fit
• Drive the deal cycle: Own every step from first pitch to signed contract, tailoring your messaging and demos to the customer's specific business and technical needs
• Listen with intent: Surface customer requirements through thoughtful, attentive conversation and clearly articulate how our AI solutions uniquely meet those needs
• Close with precision: Consistently hit or exceed your quota by managing high-quality, high-velocity deal flow across the funnel
• Navigate stakeholder maps: Understand how decisions are made and drive consensus across legal, risk, IT, and business units
• Accelerate revenue: Design and refine sales collateral, demos, and tools that speed up the path to close
• Lead pilots and transitions: Partner with Customer Success to ensure a smooth handoff and long-term adoption
• Grow accounts: Stay close to customers post-sale to identify upsell and renewal opportunities
• Build the machine: Help define the sales motion, metrics, and process as we scale
• Build the team: Recruit, onboard, and coach top-tier sales talent—fostering a culture of accountability, curiosity, and high performance
  
  

Requirements

• 8-10+ years in enterprise SaaS sales or management consulting with a strong record of closing complex deals
• 3+ years in a leadership or team-lead role; you're as comfortable selling as you are mentoring
• Experience selling AI, data, or technical products to financial services, insurance, or adjacent verticals
• Familiar with early-stage environments where you're expected to build the strategy, not just execute it
• Clear, confident communicator who can break down complex ideas for any audience
• Deeply curious, highly accountable, and motivated by impact
• You operate with urgency, precision, and a founder mindset
• Bachelor's degree required; MBA or technical background is a plus
  
  

Benefits

Position Location
By applying to this position, you can select your preferred working location from the following within the United States: Santa Monica, CA or New York, NY.
Compensation
TWG offers a competitive base + commission structure for this position.
TWG is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. #J-18808-Ljbffr