About Spekit

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, as well as America’s Best Startup Employers in 2026 by Forbes, 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

Spekit is building the revenue enablement solution for the AI-powered future. We're looking for the strategically-aligned sales leaderto take us there and then keep scaling with the opportunity to grow the team and this role.

This year is all about making our team a high-focus, high-execution selling machine in the mid-market and enterprise space. You bring your execution expertise to coach in the deals with our current and to-be-hired AEs to drive best-in-class results throughout the entire process: prospecting, qualifying, deal management, and closing.

You'll be a key partner across the org, especially with the Marketing and Customer Success teams to find high-fit customers who buy, grow, renew and become long-term partners and evangelists of Spekit.

We are very enthusiastic about candidates based in the Denver area but are open to strong applicants elsewhere in the US.

We cannot consider candidates outside of the US who wish to work remotely, or who need sponsorship to work in the US.

Location: Strong preference for Denver, CO. In office 2x per week. Open to remote locations within the US

What You'll Do

Hands-On Coaching & Team Development

• Directly manage and develop a team of sales reps - riding deals, reviewing calls, giving real-time feedback, and building a coaching cadence that drives measurable performance improvement.

• Set a high bar and give reps the support to meet it. You hold people accountable and invest in their growth - those aren't in tension here, but are the same thing.

• Hire and ramp new sales talent with a clear onboarding process within Spekit, and key milestones to hit, that gets reps productive faster. Present a clear thesis and POV on what makes a great sales rep and hire to that belief.

• Build toward managing managers over time, but earn that by establishing a team and culture worth scaling first.

• We have a compelling and competitive product that requires a challenger sales mindset and a drive to access the business leaders in Sales and RevOps to maximize potential - help your team to see and penetrate accounts to drive success.

Process & Deal Execution

• Partner with Marketing to drive pipeline, but truly own the outbound execution for reps. Bring your proven outbound motion and approach to build a pipeline machine with clear rep accountability to ensure your team consistently hits 30-40% outbound pipeline creation goals, utilizing automation to prospect smarter and faster than the competition.

• Enforce a sales process that reps adopt because it makes their jobs easier and their deals more winnable. Use clear stage criteria, qualification frameworks, and exit conditions to give both reps and leadership an honest picture of the pipeline at all times.

• Anchor every deal review on ICP fit as a primary signal. We've learned that strict ICP discipline is the driver of win rates, velocity, and conversion - and it also sets up customers for long-term success. Deals that don't fit the ICP don't move forward, and that's a feature, not a bug.

• Run a rigorous, accurate forecast - and coach reps to do the same. Every rep should understand that maths behind hitting their targets and be held accountable to them.

AI & Tooling

• Adopt Spekit as a core part of how the team operates: ensuring reps always have the right playbooks, competitive intel, and answers in the flow of work. We build this for revenue teams - you'll be our best internal proof point.

• You lead by example by being on the absolute forefront of AI experimentation. You are building your own custom agents, testing LLM prompts, and architecting agentic workflows to push the boundaries of what’s possible.

• You use AI and automation to scale your own capacity, surfacing hidden deal risks and coaching at scale.

Marketing & CS Partnership

• Partner with Marketing to drive maximum value from leads and pipeline including ICP definition, pipeline quality, campaign alignment and feedback to make sure campaigns optimize for results. Collaborate with Marketing to ensure "full-court press" on inbound and effective design and execution of outbound and ABM campaigns.

• Partner with Customer Success to ensure sales is winning the right customers. ICP fit isn't just a sales metric - it's the foundation of retention and expansion. Co-own the definition of a great customer with CS leadership, and make that definition visible in how you qualify and review deals.

Strategy & Leadership

• Partner with our CEO and COO on go-to-market strategy, revenue targets, and building the operational foundation for scalable growth.

• Communicate pipeline health, performance trends, and risks to leadership with clarity and honesty - including when the news is hard.

Who You Are

• A proven sales leader in B2B SaaS with a track record that includes strong win rates, healthy pipeline conversion, and teams that didn't just hit number - they hit the right numbers with the right customers.

• Fierce Challenger Sales DNA: You don’t just "manage" a sales process; you redefine how the customer thinks about their problem. You are a Challenger Seller at heart, comfortable creating healthy tension and leading prospects to the "cost of inaction." You have proven experience creating high-performing sales teams that thrive as the underdog and have a proven track record of entering established markets and dismantling the status quo with a superior, new approach.

• A coach who gets results through people. You can point to specific reps you've developed and tell that story clearly. You give feedback that lands, you identify where someone is stuck, and you help them move.

• Disciplined on ICP. You've seen what happens when sales chases the wrong deals, and you've built or operated within a process that holds a firm line. You know that saying no to the wrong deal is as important as winning the right one.

• Hands-on with AI and sales technology. You've built your AI tools (ie. gems, agents), used tools like Gong, AI-assisted forecasting, or automation platforms in previous roles - ideally including Spekit - to help reps work cleaner and move faster. You don't wait for someone to hand you a playbook; you experiment and build.

• A cross-functional partner, not a silo. You've built strong working relationships with Marketing and CS grounded in shared goals and honest communication. You don't protect territory - you build pipeline.

• Data-sharp. You can look at a pipeline and tell a story - where the risk is, where conversion is breaking down, and what to do about it. Your reps know their numbers because you've made that a cultural expectation, not just a reporting requirement.

• Scrappy and scalable. You're energized by a lean environment where you're doing the work yourself today, and you have the experience and vision to know how to grow the team around you over time.

We've got you covered!

• 🩺 100% paid employee Medical, Dental, Vision, and Life Insurance. Benefits begin on your first day!

• 💸 Meaningful equity

• 🌴 Flexible Paid Time Off (PTO) policy

• 🤒 Sick time pay

• 🎂 Your birthday off!

• 🎉 Paid Holidays + 1 week end-of-year company shut down

• 💼 Company sponsored 401k

• 📚 Yearly Learning & Development Stipend

• 👶 Maternity/Paternity benefits (both birthing and non-birthing parents)

• 🚀 The chance to help build from the ground up – the hires we’re making now are foundational to our growth as a company!

The culture that defines us: Y O K E D

Yoke: We move as one, because that’s how we move faster and achieve more. Our speed, strength and ability to innovate lie in how we align, collaborate, support, and courageously challenge and give feedback to one another, running towards our shared mission

Own it: We think like owners. We’re proud of our work, we follow through on commitments, and we do what’s right, even when it’s hard.

Keep It Simple Yet Spektacular: We cut through complexity and relentlessly craft intuitive, fast, and delightful experiences—in our product and in how we work— to move fast, earn our own obsession, and create true, lasting customer love.

Enjoy the Journey: We laugh along the way. We’re kind to each other, we pause to embrace the moment, and celebrate the small wins, even when things get tough, because we recognize that what brings meaning to what we do is who we get to do it with.

Drive: We push to get better every day because we love what we do. Growth, curiosity, learning and innovation fuel us. We embrace feedback and the challenges in front of us, moving with purpose, intention and speed

About the Team

At Spekit, we don't just talk about creating opportunity — we build it! With two female founders and a commitment to representation in tech, we're intentional about fostering an inclusive culture, supporting underrepresented communities, and building a team that reflects the diversity of our users. You'll join a collaborative, mission-driven team building category-defining AI products that meaningfully change how people learn and work. This is a rare opportunity to build an iconic company, work directly with leadership, and see your ideas ship quickly in a high-trust environment. If you're excited by the challenge of building elegantly simple, intelligent software that solves real problems for real users, we'd love to talk.

Compensation Range: $350K - $400K