Director, Training & Enablement

We are seeking a Director of Training and Enablement who will build and operate Striim’s end-to-end training and enablement engine, including new-hire sales and technical bootcamp,  Challenger and MEDDPICC certification, internal and external Striim Academy, and more. This role supports the methodology and process-driven revenue engine capable of carrying Striim to its revenue goals over the next 12 – 18 months.

• Sales Methodology: Roll out Challenger + Value Selling + MEDDPICC across AE/GAE/ SE/FE. Personally design the certification curriculum, deliver the first cohort, and run weekly Gong-based coaching with sales leadership. Build the Challenger Teaching Pitch library for each of three GTM motions: Application & Data Modernization, Event Stream Processing, Contextual Data Engine for Enterprise AI.
• New-Hire Bootcamp: Design and operate the 30/60/90 onboarding program for new AE/GAE/SE hires in 2026. Build stage-by-stage playbooks by GTM motion, Use Case, industry verticals (Financial Services, Healthcare, Retail), and persona profile (CIO, CDO, Enterprise Data Architect, DBA, Data Engineer). Own ramp certification gates.
• Striim Academy (internal + external): Stand up the internal Academy with courses you build in our LMS with role-based learning paths. Launch the external Striim Academy - developer, customer, and partner certifications, hands-on labs, digital badges, and build a community funnel. Deliver a 10-module curriculum across Striim Platform and Validata tracks.
• Learning Tech Stack: Own and operationalize the approved learning stack: WorkRamp (LMS), HighSpot, Claude Cowork (content), Gong AI (call coaching, methodology adherence scoring), Reprise (Demo platform), and implement knowledge surfacing in Salesforce / Slack), sunset Mediafly + redundant WorkRamp gaps.
• SKO & Operating Cadence: Co-own delivery of the July 2026 Sales Kick-Off (Challenger Boot Camp combined with Whiteboarding across the three GTM motions by personas, industries and use cases). Run the bi-weekly enablement Sales Scoops, the monthly marketing campaign support motion, and the quarterly technical and sales certification waves.
• Partner & Co-Sell Enablement: Build partner-readiness curriculum for GCP and Microsoft Azure co-sell motions (ACR / MACC alignment). Partner closely with Partner Technology and Alliances. Treat hyperscaler AEs as a second sales force we enable.

• 8+ years' B2B enterprise sales enablement experience, with at least four years at a director or head of level.
• Personally certified to deliver Challenger Sales (Gartner / CEB certified, or equivalent train-the-trainer credential), including proven experience successfully implementing Challenger across at least one full sales organization, not just having been trained in it.
• Hands-on implementation of Sales Playbooks in Salesforce: you have personally designed the fields, the scoring logic, and the stage-gate enforcement. You can talk through what works and what falls apart at adoption.
• Built and scaled a learning function within a high-growth B2B enterprise technology organization focused on cloud infrastructure, distributed systems, data platforms, real-time streaming, developer tooling, database technologies, and modern data integration ecosystems, typically in the $25M–$150M ARR range.
• Track record of operating both internal sales enablement and an external academy. You understand why developer education is a demand-generation channel, not a cost center.
• Comfort with AI-augmented content workflows. You have used Claude, ChatGPT, Gong AI, or equivalent in production - to generate first drafts, score calls for methodology adherence, or build adaptive learning paths. You can tell the difference between AI output that ships and AI output that needs to be rewritten.
• Execution Role. You will build decks and training modules, deliver workshops and Sales Scoops, and review Gong calls, creating and delivering reports and feedback to the team. You are not looking for a role where you only manage.

• Operated inside a hyperscaler co-sell motion - GCP, Microsoft Azure, or AWS and understand MACC / ACR consumption credit as a demand-generation lever.
• Built or led an external developer certification program at scale (Confluent Developer Skills Path, MongoDB University, HashiCorp Certified, GitLab Certified, Databricks Academy).
• Domain background in change data capture, app/data modernization to cloud, streaming analytics, or hyperscaler technology.
• Hands-on operator experience with the Striim stack: WorkRamp, Highspot, Gong AI, HighSpot, Reprise, GoldCast.
• Has built a value-engineering or ROI calculator that sellers actually use in deals.
• Has run a Sales Kick-Off as the primary owner, not just a presenter.

• Competitive salary and pre-IPO stock options
• Comprehensive health care plans (medical, dental and vision), including medical and dependent FSA
• Paid Time Off (Vacation, Sick & Public Holidays)
• The chance to contribute to and shape an upbeat, fully engaged culture

$150,000 - 160,000 USD on an annualized basis with a chance to earn additional variable.

Applications will be reviewed on a rolling basis and accepted until the position is filled.