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Kyle Williams

@kylewilliams2

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I am a sales training leader designing AI-enabled curricula that shorten ramp time and improve close rates.

United States

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What I'm looking for

I seek a data-driven sales enablement or training leadership role where I can build AI-powered curricula, shorten ramp time, and deliver measurable lift in close rates within collaborative, compliance-aware teams.

I am a sales training and enablement leader with a practitioner background in consultative selling and a decade-plus of front-line sales experience. I design and deliver instructor-led and AI-powered curricula that reduce ramp time and lift conversion.

At enterprise and contact-center scale I have built 6-week onboarding programs for ~150 reps, authored LMS content, and implemented Kirkpatrick-aligned pre/post/30-day certification that cut time-to-first-sale by 32%.

I founded and product-architected ObjectionOS, an objection-intelligence simulation using multi-model prompt flows and AWS deployment (Lambda, API Gateway, S3) to deliver p95 latency under 300ms and reduce user error by over 80%. I pair product work with Power BI dashboards and scorecards to drive Level-4 managerial insights.

I bring a data-driven, compliance-aware approach—aligning scripts and SOC2-aligned prompt governance—while coaching cohorts and facilitating role-plays that consistently earn high facilitator ratings and drive measurable business outcomes.

Experience

Work history, roles, and key accomplishments

Current

Founder & Product Architect

Current

ObjectionOS LLC

Feb 2025 - Present (6 months)

• Conceived/built a real-time Objection Intelligence simulation for reps to rehearse high-stakes objections pre-call.
• Engineered multi-model prompt flows (GPT-4o/Claude/Llama) with JSON-schema enforcement, adaptive personas, and a fuzzy-command layer that reduced user error >80%.
• Deployed on AWS (Lambda, API Gateway, S3); published white paper; led pilot within a top national accounting firm.

Prompt Engineering GPT 4o AWS Lambda API Gateway S3 Simulation

AI Program Lead - Sales

1-800 Accountant

Jan 2025 - Jul 2025 (6 months)

• Directed rollout of ObjectionOS across Sales/SDR/Retention; authored SOC 2-aligned prompt
policy and script governance map to regulated environments; coordinated SSO with Engineering.
• Built Power BI dashboards surfacing confidence scores, objection types, and win-rate trends to
give managers Level-4 insights.

Training Specialist & Nesting Manager

1-800 Accountant

Jan 2025 - Jul 2025 (6 months)

• Built and delivered a 6-week onboarding across ~150 reps (consultative discovery, objection handling, service recovery) using ILT, team exercises, AI-powered sims, role-plays, and knowledge checks. Created new LMS content or updated all outdated LMS modules.
• Implemented Kirkpatrick-aligned pre/post/30-day certification → ramp-to-first-sale down 32% (28 → 19 days).

Project Management Sales Communication Skills Training Development AI Training Sales Training Training Delivery Model Training

Small Business Tax Expert

1-800 Accountant

Oct 2023 - Jan 2025 (1 year 3 months)

• Closed $350K+ ARR (bundled SaaS + advisory); top 5% close rate within a 100+ rep floor.
• Full-cycle selling; maintained Salesforce hygiene, pipeline forecast accuracy, and 30-day
post-purchase account support.

Associate Director of Admissions

Cortiva Institute

Feb 2023 - Oct 2023 (8 months)

• Turned lowest-performing campus into #1/15 in six months: tours +42%, same-day apps +37%, conversion +19 pts.
• Introduced daily pipeline stand-ups and flash trainings; ramp trimmed 4 wks → 2.5 wks.

Sales Communication Skills Objection Handling

Training Specialist

Saint Leo University

Jan 2020 - Feb 2023 (3 years 1 month)

• Authored a 30-module onboarding; ramp 45 → 27 days during the 30-day COVID remote pivot.
• Managed remote nesting cohorts (6–15), facilitating LMS modules we designed.
• Drove +18% graduate inquiries YoY; conversion +12%.

Project Management Sales Communication Skills Training Development Sales Training Training Delivery