About Spekit

At Spekit, we’re building a truly context-aware experience where you never have tosearch for the right answer again. It starts withSidekick, 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 aVisionary 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.

Role Overview

We’re looking for an Account Executive who thinks strategically, understands how AI is changing go-to-market teams and processes, and wants to influence messaging, systems, and pipeline strategy — in addition to closing deals.

The Account Executive role is responsible for driving new revenue by owning and executing a full-cycle sales motion for strategic mid-market customers (approximately 300–3,000 employees). This role requires strong discovery skills, sound judgment, and the ability to align customer needs with Spekit’s solutions through consultative, strategic selling.

Account Executives are expected to operate independently while partnering closely with Sales Leadership, Customer Success, and cross-functional teams to close new business and support renewals and expansion opportunities.

The role reports to the VP of Sales,Evan Horibe.

This role is built for sales reps who:

Want to bring cutting edge AI-products to market. Not just sell features, but help define how AI reshapes go-to-market teams and revenue workflows.
Think strategically about AI in sales. You understand how automation, copilots, agents, and contextual intelligence change pipeline generation, deal velocity, and rep productivity.
Don’t just run the playbook — you influence it. You want a seat at the table shaping messaging, positioning, and how we sell an AI-first platform in a rapidly evolving market
Operate as a consultative advisor, not a demo jockey. You lead high-value discovery conversations around workflow inefficiencies, AI adoption strategy, and revenue transformation.
Are relentlessly resourceful and adaptable. In a world where the tech shifts monthly, you learn fast, think critically, and turn ambiguity into opportunity.
Care deeply about customer outcomes. You’re obsessed with helping teams move faster, work smarter, and unlock leverage through intelligent systems — not just closing a deal and moving on

What you'll do:

Own and manage a pipeline of strategic mid-market accounts
Execute full-cycle sales activities, including prospecting, discovery, solution alignment, negotiation, and closing
Generate and manage a portion of personal pipeline through outbound prospecting and account development
Conduct regular, sustained communication with prospects and customers via phone, video conferencing, and email
Lead complex sales conversations, handle objections, and negotiate commercial terms and contracts
Achieve and consistently meet or exceed assigned sales targets and performance expectations
Partner with Customer Success on renewals and expansion opportunities
Navigate multi-stakeholder sales cycles and sell to multiple levels within customer organizations, including executive leadership
Exercise consistent judgment and decision-making when engaging C-level stakeholders and managing strategic deals
Prioritize tasks effectively and manage time in a fast-paced, quota-driven environment
Maintain accurate pipeline and activity tracking in Salesforce and related systems
Collaborate as a team player and contribute positively to team culture and shared goals

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 (though not required) 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

We've got you covered!

🩺100% paid employeeMedical, 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 sponsored401k

📚 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 YetSpektacular: 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.

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