Director of Sales Enablement

Inspira Education

About The Position

Inspira Education Group is a rapidly growing edtech startup dedicated to democratizing access to high-quality coaching. As a leading network of admissions coaches, we are disrupting traditional application processes with innovative products and services. Backed by prominent venture capital firms, we are seeking a strategic and collaborative Director of Sales Enablement to scale our go-to-market organization. This role involves partnering across various departments to equip customer-facing teams with the necessary knowledge, tools, processes, and content to enhance customer experience and drive business results. The Director will act as a liaison within the GTM organization, translating strategy into execution, identifying performance gaps, facilitating product launches, and developing scalable programs to boost sales effectiveness and customer outcomes. This position is ideal for someone who enjoys solving sales challenges, influencing cross-functional teams, and creating programs with measurable impact.

Requirements

Prior experience carrying an individual sales quota or serving in a consultative customer-facing role (Sales, Business Development, Account Management, Customer Success, Retail Leadership, or similar). You understand firsthand what it takes to build trust with customers, navigate objections, and operate in a performance-driven environment.
3+ years of experience in a customer-facing revenue role and/or Sales Enablement, Revenue Enablement, Sales Operations, Product Marketing, or a related GTM function.
Experience designing and scaling enablement programs that improve onboarding, sales readiness, product adoption, or customer experience.
Proven ability to build trusted partnerships across Sales, Product, Product Marketing, Marketing, Revenue Operations, Customer Experience, and executive leadership.
Excellent communication and facilitation skills, with the ability to simplify complex concepts and influence audiences ranging from frontline employees to senior leaders.
An analytical mindset with experience using performance metrics, customer feedback, and business insights to identify opportunities and measure the impact of enablement initiatives.
A builder's mentality—you enjoy creating scalable programs, playbooks, and processes that help teams perform at their best.
High emotional intelligence and credibility. You listen before prescribing solutions, seek to understand the realities of frontline teams, and earn trust through empathy, collaboration, and thoughtful execution.

Nice To Haves

Experience in a direct-to-consumer, retail, consumer technology, marketplace, or high-growth environment.
Experience supporting product launches and go-to-market initiatives across multiple customer-facing teams.
Familiarity with CRM platforms (Salesforce, HubSpot, or similar), learning management systems, and enablement tools such as Gong, Highspot, Seismic, WorkRamp, or similar platforms.
Experience coaching managers or facilitating leadership development programs.

Responsibilities

Design, build, and continuously improve onboarding programs to accelerate new-hire ramp time.
Develop ongoing training programs that strengthen product knowledge, consultative selling, objection handling, and customer experience.
Create certifications, learning paths, coaching resources, and sales enablement programs.
Analyze sales performance trends and identify opportunities for targeted enablement initiatives.
Analyze conversion, win/loss, and retention data to identify what's working and feed it back into training.
Review call recordings and customer interactions to surface best practices from top performers and turn them into repeatable playbooks.
Track and report on enablement-specific metrics and their downstream impact on conversion or win rate.
Partner with Product Marketing to translate positioning, messaging, and competitive insights into practical sales playbooks, talk tracks, FAQs, and customer-facing resources.
Collaborate with Product Management to prepare customer-facing teams for product launches by developing training, enablement content, and readiness plans.
Work closely with Marketing to ensure campaign messaging is consistently reflected throughout the customer journey.
Partner with Revenue Operations to support CRM adoption, process improvements, sales workflows, and operational readiness.
Collaborate with Customer Experience and Customer Success teams to improve onboarding, retention, upsell, and support experiences.
Gather frontline feedback and communicate customer insights back to Product, Marketing, and Sales Leadership to continuously improve our GTM strategy.
Create and refine high-converting playbooks, call scripts, objection-handling guides, and cross-sell/upsell matrices for the sales team.
Own the organization and maintenance of sales enablement content, including playbooks, product documentation, competitive battle cards, sales presentations, and knowledge resources.
Ensure customer-facing teams have easy access to current, accurate, and actionable enablement materials.
Package customer proof points, case studies, and FAQs into reusable assets teams can pull from in the moment.
Develop scalable communication plans for product launches, process updates, and organizational changes.
Own or co-own enablement tooling (e.g., CRM/helpdesk macros, content/asset libraries, call recording platforms) so teams can find the right resource in seconds, not minutes.
Partner with RevOps to keep CRM data clean and process consistent across teams.