At Spekit, we’re building a truly context-aware experience where you never have to search for the right answer again. It starts with Sidekick, our execution layer that lives in your browser, Slack, and beyond. Sidekick anticipates a sales rep’s next move, translating complex signals into in-flow coaching, automated workflows, and deal-aware content creation — constantly answering the only question that matters:
“Given everything I know about this deal, what should I say, share, or do right now?”
But delivering that experience requires more than a chatbot. It requires an authoritative system of truth that governs how a company goes to market. A content platform that keeps information dynamic and accurate as the business evolves, connecting enablement to real revenue outcomes. An intelligence layer humans rely on, and the one other AI systems consume. It requires, Spekit.
Recognized as a Visionary in Gartner’s 2025 Magic Quadrant for Revenue Enablement Platforms, we’re reimagining how people work and learn in an AI-first world. Come build with us!
Backed by: $60M+ from Craft Ventures, Felicis, Foundry Group, and Renegade Partners
Trusted by: A 2025 Gartner Visionary powering teams at Southwest Airlines, Justworks, Equifax, and FlorenceHQ.
About the Role
We're looking for a sharp, creative, and technically fluent individual to partner with our Sales Solutions team to bring Spekit to life for prospects and customers. Sitting on the Customer Success team, you'll be responsible for building custom demo environments and proof-of-concept orgs that feel like they were built for the account sitting across the table.
You'll be using the latest AI tools to translate a customer’s business context it into a polished, compelling Spekit demo environment that makes the "aha moment" impossible to miss. You have a designer's eye, a consultant's business instincts, and enough familiarity with AI and LLMs to move fast without sacrificing quality.
Custom Demo & Org Design
Build and maintain tailored Spekit demo orgs scoped to specific prospects, verticals, and use cases — from initial discovery through to live presentation.
Recreate and adapt real customer content (playbooks, battlecards, deal rooms, training docs) into polished Spekit-native formats that feel authentic and relevant.
Design topic structures, Spek libraries, and learning paths that reflect how a prospect's actual team would work — not a generic out-of-the-box setup.
Iterate quickly based on feedback from AEs and SEs, turning around org updates on tight timelines.
Scoping & Business Context
Partner with Head of Solutions and Account Executives to understand prospect business needs, sales motions, and key personas before building anything.
Translate discovery notes and call recordings into a clear org design brief — identifying what content to build, what workflows to demonstrate, and what "moments that matter" to surface.
Bring a high degree of business acumen to every build: you understand why enablement matters to a VP of Sales differently than it does to a Sales Ops lead, and you design accordingly.
AI-Assisted Content Creation
Leverage AI tools and LLMs to build agents and automation to make your job easier.
Leverage agents to generate, adapt, and scale content creation — turning a handful of source materials into a full, realistic org faster than anyone expects.
Use Spekit's AI Content Builder (HTML editor) tools fluently, and push their limits to see what's possible.
Develop reusable templates, prompt libraries, and build patterns that make future demo orgs faster without making them feel templated.
Quality & Craft
Own the visual and experiential quality of every org you ship — content should be well-written, logically structured, and designed to guide a viewer naturally through the story.
Maintain a library of demo assets across verticals and personas that the broader GTM team can draw from.
Identify gaps in out-of-the-box templates and work with internal teams to improve them.
Experience
Background in instructional design, sales enablement, solutions engineering, or a related technical field (ie. you understand how to work with AI)
Experience building demos, configuring SaaS platforms, or designing customer-facing content environments.
Comfortable working in a fast-paced pre-sales environment where priorities shift and timelines are tight.
Skills & Strengths
Strong design sensibility, you notice when something looks off and you fix it; you think about hierarchy, flow, and how someone will experience what you've built.
High business acumen, you can read a prospect brief and immediately understand what will resonate with their leadership and their reps.
Hands-on familiarity with AI tools and LLMs, you use them daily to accelerate your work, not occasionally to experiment.
Excellent written communication, the content you build needs to sound like it came from the prospect's own team, not a generic vendor.
Detail-oriented without being slow, you hold a high bar for quality and you're also resourceful enough to hit the deadline.
In your first 60 days, you'll have built several custom demo orgs from scratch, developed a strong sense of Spekit's core use cases across verticals, and established a workflow with the SE and AE and CS team for scoping and delivering builds efficiently.
Within six months, your orgs will be a recognized asset in competitive deals — prospects will comment on how tailored and polished the experience felt. You'll have a growing library of reusable components that make every new build faster.
Within a year, you'll have meaningfully influenced win rates through the quality of demo experiences, contributed to how the broader team thinks about org design and content standards, and become the go-to person for turning a business problem into a Spekit story.
