About the Role
We are seeking a Senior Director of Sales Enablement & Intelligence to build and scale our Sales IQ function—our integrated approach to sales intelligence, enablement, and performance analytics.
Sales IQ is the engine behind how our sales organization wins. It brings together market insights, data-driven performance management, and field enablement to ensure our teams are equipped with the right tools, messaging, and strategies to succeed in a highly competitive title insurance landscape.
This role sits at the center of our revenue organization, translating market signals and sales data into actionable insights, scalable programs, and consistent execution across a geographically distributed sales team. You will define how we go to market, how we measure success, and how we continuously improve performance.
This is a highly visible role with the opportunity to build from the ground up—shaping strategy while also rolling up your sleeves to drive execution.
Responsibilities
Sales Intelligence & Market Insights
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Build and maintain a competitive intelligence program covering title insurance agents, real estate brokers and agents, builder channels and lender driven title
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Deliver actionable market analysis, remittance trends, regional dynamics, competitor positioning—to inform territory planning and pursuit strategies
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Partner with Sales, Marketing, Technology, and Finance to translate market signals into positioning and messaging
Sales Enablement & Content
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Own the sales playbook: objection handling, value propositions, vertical-specific talk tracks, and proposal templates
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Develop and curate a content library aligned to buyer journey stages and channel segments
Performance Analytics & Reporting
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Define and track KPIs across the sales funnel—pipeline velocity, win rates, average order value, retention
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Build dashboards and reporting cadences that give field leaders visibility into team and individual performance
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Identify performance gaps and partner with regional directors on targeted coaching and intervention
Sales Technology & Tools
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Own the sales tech stack (CRM, CPQ, enablement platforms) and drive adoption across the field
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Evaluate and implement tools that improve productivity, forecast accuracy, and customer engagement
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Ensure data hygiene and process compliance to support reliable reporting
Cross-Functional Partnership
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Collaborate with Marketing on campaign execution, lead management, and ABM initiatives
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Work with Operations and Underwriting to streamline quoting, pricing, and deal desk processes
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Serve as the connective tissue between corporate strategy and field execution
Qualifications
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10+ years in sales enablement, sales operations, or revenue intelligence roles—ideally within title insurance, mortgage, real estate services, or financial services
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Proven experience supporting a distributed sales model with regional teams selling through multiple channels (lenders, realtors, builders, commercial)
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Strong analytical and strategic thinking skills, with the ability to translate data into action: comfortable building models, interpreting funnel data, and presenting insights to executives
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Proven ability to develop training programs, playbooks, and content that drive measurable sales improvement
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Hands-on experience with CRM platforms (Hubspot preferred), BI tools, and sales enablement software
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Excellent communication skills—able to influence without authority across a matrixed organization
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Bachelor's degree required; MBA or advanced degree a plus
What Sets You Apart
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Deep understanding of title insurance products, underwriting basics, and the competitive landscape
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Track record of building a sales enablement or Sales IQ function from the ground up
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Experience integrating marketing automation with sales workflows
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Familiarity with real estate transaction cycles and seasonal demand patterns
What Success Looks Like
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A scalable Sales IQ function that drives consistency and performance across regions
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Clear visibility into sales performance through actionable dashboards and reporting
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Improved ramp time, pipeline conversion, and win rates
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Strong adoption of tools, processes, and playbooks across the field
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A more data-driven, accountable, and aligned sales organization
Compensation & Benefits
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Competitive base salary + annual bonus
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Comprehensive health, dental, and vision coverage
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401(k) with company match
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Flexible PTO and remote work options
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Professional development budget
About TRG
TRG is one of the nation’s largest and fastest-growing title insurance underwriters, delivering trusted solutions to a broad range of customers and protecting property ownership rights across America. At TRG, we don’t just underwrite title insurance policies – we build partnerships that last.
As part of our broader network, we proudly serve leading affiliate partners, including Anywhere Real Estate, Inc. a subsidiary of Compass, Inc. (d/b/a Compass International Holdings) (NYSE: COMP), HomeServices of America (a Berkshire Hathaway affiliate), Lennar (NYSE: LEN and LEN.B), and Opendoor Technologies Inc. (NYSE: OPEN) – and a large network of strong independent agents.
We are powered by our people—their expertise, dedication, and passion drive everything we do. As a Great Place to Work®-certified company, we believe our employees are our greatest asset. Your success drives ours, and at the core of our company is a commitment to help you own, develop, and nurture your career.
Why Work with Us?
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Lead in the Industry:Join one of the nation’s largest and fastest-growing title insurance underwriters.
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Powered by Our People:Be part of a team where your talent and ideas fuel innovation and success.
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Innovate for Impact:Create solutions that solve real problems and deliver value to customers.
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Culture Where Every Voice Counts:Work in a positive, inclusive, and collaborative environment where your ideas matter.
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An Edge for Your Career:Access tools, resources, and training designed to helpgreat talentbecome even stronger.
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Advancement Opportunities:Take on new opportunities to expand your skills and grow.
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Flexibility That Fits:Enjoy remote and hybrid options (role-dependent) to support work-life balance.
For more information, visit www.TRGUW.com.
