Sales Enablement Principal - AI Conversation & Sales Simulation

Inovalon•Bowie, MD

21h

About The Position

The Principal AI Sales Simulation & Enablement Manager is a senior individual contributor responsible for designing, implementing, and scaling a blended AI‑driven and enablement‑led sales readiness ecosystem. This role strengthens seller execution and frontline sales manager effectiveness through conversational intelligence, simulation, certification, training, and performance‑based enablement programs. This position does not manage people. Instead, it operates as a high‑impact IC who leads through expertise, influence, and ownership, partnering cross‑functionally with Sales Leadership, Revenue Operations, Product Marketing, and Sales Excellence. Approximately 50% of the role will be focused on AI-based initiatives including overseeing the rollout of a conversational intelligence solution. The remaining 50% is dedicated to broader sales enablement, training strategy, and performance alignment. The ultimate objective is to translate skill‑building into measurable improvements in stage conversion, forecast accuracy, time‑to‑ramp, quota attainment, and revenue bookings.

Requirements

Bachelor’s Degree in Arts/Sciences (B.A./B.S.) in a relevant field or equivalent experience required
8+ Years of experience in Sales Enablement, Sales Training, or Revenue Operations, with demonstrated experience driving technology-enabled training at scale required
Demonstrated proficiency working with Conversational Intelligence Tools (e.g., Gong, Chorus, Attention)
Demonstrated proficiency working with AI-based sales simulation tools (e.g., Hyperbound, Quantified, Yoodli, Second Nature, Pitch Monster, Outdoo, or similar platforms).
Experience leveraging conversational intelligence systems to inform training scenarios using real-world deal data and call recordings.
Strong understanding of B2B sales cycles, particularly within mid-market environments.
Demonstrated ability to translate data insights into actionable skill development strategies.
Experience designing certification frameworks tied to measurable performance standards.
Strong analytical capability with experience linking learning initiatives to performance metrics such as win rates, conversion rates, quota attainment, forecast accuracy, and booking impact.
Ability to influence and drive changes across sellers, frontline managers, and sales leadership.
Strong project management skills with the ability to prioritize, execute, and iterate in a fast-paced environment.
Proficiency with CRM systems, LMS platforms, and modern enablement technology stacks.
Ability to work both independently and collaboratively with Sales Leadership, Product teams, and cross-functional stakeholders.
Ability to thrive in a dynamic, high-growth environment with changing priorities and tight timelines.

Responsibilities

Drive adoption and usage of conversational intelligence across sales and sales management.
Codify best practices and plays identified from conversational intelligence and AI sales simulation data into onboarding, training content and certifications.
Design, launch, and scale an AI-driven sales simulation library aligned to the organization’s selling motion, including discovery, demo execution, objection handling, competitive positioning, and closing scenarios.
Develop structured certification tracks tied to priority sales plays, ensuring sellers can consistently articulate value, ROI, and differentiation while effectively navigating objections.
Establish scoring benchmarks and proficiency standards that clearly define readiness to advance and certification completion.
Drive adoption and participation across targeted seller cohorts, achieving high levels of influence, enablement, and clear performance tie-ins.
Develop AI-based simulation programs for frontline sales managers focused on deal inspection, forecast calls, coaching conversations, and performance management scenarios.
Improve forecasting discipline and coaching consistency through simulation-based leadership development.
Align simulation metrics to define business outcomes, including stage-to-stage conversion rates, win rates, quota attainment, bookings growth, and time-to-ramp.
Build reporting dashboards and performance frameworks linking simulation performance data to CRM and revenue outcomes.
Own platform administration, governance, and cross-functional alignment to ensure simulation becomes embedded within sales culture.
Own administration, configuration, and governance of AI simulation platforms, ensuring scalability and compliance.
Design and scale role-based enablement programs for seller readiness, frontline manager enablement, and ongoing enablement.
Design and scale role‑based seller enablement—integrated with onboarding and career transitions—that standardizes discovery, value messaging, and sales play execution while reinforcing ICP focus, persona‑based selling, and differentiated positioning.
Develop enablement that elevates frontline manager performance by strengthening coaching, pipeline inspection, and forecast rigor through structured learning and certification, while influencing behavior with data‑driven tools and frameworks despite having no direct authority.
Own priority sales plays and GTM initiatives by partnering with Product Marketing to build training and simulations grounded in real buyer dynamics, continuously refining content based on deal data, ICP shifts, and field feedback.
Work with Sales Operations and key partner to integrate Conversational Intelligence and AI simulation tools with CRM, LMS, and relevant sales technology platforms where feasible.
Connect enablement to revenue by defining learning‑to‑performance measurement models, partnering with Revenue Operations to embed insights into forecasting and business rhythms, and equipping Sales Leadership with data‑backed visibility into skill gaps, coaching needs, and enablement ROI.
Own the full enablement content lifecycle across platforms by maintaining relevance, consistency, and clarity while reducing seller cognitive load and retiring outdated or low‑impact materials.
Coordinate simulation, certification, and readiness standards across the sales organization by influencing Sales Leadership, Revenue Operations, Sales Excellence, and Product Marketing through data, credibility, and business impact—driving cross‑team alignment without formal authority.
Continuously refine and personalize simulation scenarios using deal data, competitive insights, ICP segmentation, and field feedback.
Fulfill additional responsibilities as reasonably assigned to support operational excellence and revenue growth.
Maintain compliance with Inovalon's policies, procedures and mission statement.
Adhere to all confidentiality and HIPAA requirements as outlined within Inovalon's Operating Policies and Procedures in all ways and at all times with respect to any aspect of the data handled or services rendered in the undertaking of the position.
Fulfill those responsibilities and/or duties that may be reasonably provided by Inovalon for the purpose of achieving operational and financial success of the Company.
Uphold responsibilities relative to the separation of duties for applicable processes and procedures within your job function.