About Spekit

Spekit is the modern, AI-powered enablement platform built around context — redefining how revenue teams learn, act, and sell.

We believe the future of effective AI systems depends on governed, dynamic content — knowledge that’s structured, explainable, and always in context. That’s why Spekit unifies content management, enablement, and personalized guidance into one intelligent system that understands a company’s GTM data model, sales process, and the relationships between content, workflow, and outcomes.

At the core is AI Sidekick, the Just-in-Time Sales Assistant™, which leverages signals from CRM, call intelligence, and communication tools to deliver real-time recommendations, adaptive guidance, and automated workflows — directly within a rep’s flow of work. Sidekick’s contextual AI agents continuously learn from governed content and rep activity, turning static documentation into living, actionable intelligence that drives consistent execution at scale.

Backed by leading investors including Craft Ventures and Felicis, Spekit has raised over $60M and is trusted by world-class organizations like GitLab, ZoomInfo, Southwest Airlines, Equifax, and more to power their enablement in the flow of work.

The Opportunity

If you’re reading this, it means you’re at least considering the idea of ditching your current 9-5 and looking for a place where you can help build something BIG. Look no further, have we got a challenge for you.

We’re looking to expand our sales team by hiring a seasoned Sales Executive to grow our customer base in the mid market space (100- 5000 employee count). But this isn’t like any other sales role. On this team, your job is to determine what the prospect thinks they need and then align it with what they really need. How? By asking the right questions, understanding the customer goals & aspirations, and customizing their experience with a genuine interest for the growth of the prospect’s business. This is a strategic selling opportunity where your discovery process, thorough understanding of the market, creative problem solving and storytelling abilities will be put to the test.

Our small but mighty sales team currently reports into our Head of Sales, Freddy Daues. This is a full-cycle sales motion, meaning our sales reps are responsible for generating their own pipeline, working deals through the sales cycle, negotiating contracts and closing deals. Sales reps also partner with our customer success team on renewals and expansion opportunities.

What You’ll Do

Own and manage a pipeline of Mid Market and Enterprise clients
Question, consult, educate, strategize, and successfully sell Spekit through a mix of outbound prospecting techniques – strong communication and tenacity are key!
Adapt product recommendations quickly to suit prospect’s needs – asking probing questions and handling objections will be critical to your success
Achieve and consistently exceed assigned sales goals

What We’re Looking For in You

You’re hungry to bring a new product to market and close big deals!
You’re excited to shape the sales strategy and bring in new revenue for a young, rapidly growing startup
You know how to build a sales pipeline and you love managing the full sales cycle
You have a client first mentality and are passionate about helping companies find solutions to their toughest problems
You are adaptable and can think on your feet.
When faced with new challenges, or tough conversations, failure simply isn’t an option

Must-Haves

5+ successful years as a quota carrying Account Executive in B2B SaaS Sales
You have experience bringing new product(s) to market - ideally in the broader learning or enablement space which includes selling to enablement teams, sales leaders and/or revenue operations teams
You have proven experience in closing deals and consistently exceeding sales quotas
Comfortable with high-end exposure to C-level executives, and the ability to build strong trusted relationships
Ability to perform a full lifecycle sale from prospecting to closing
Experience navigating complex sales cycle, with the ability to sell to multiple levels and through an organization
Detail-oriented and analytical with a high clock speed
Proven experience nursing a deal through a 1-6 month sales cycle
Team player, positive attitude and willingness to help others
Ability to influence key decision-makers and negotiate effectively
Comfortable with Salesforce
Ability to effectively prioritize tasks and manage time within a fast-paced environment
Must be able to work legally in the US