Opportunities at Craft portfolio companies


Head of Sales



Sales & Business Development
Denver, CO, USA
Posted on Wednesday, February 28, 2024
Our Mission
Headquartered out of Denver, CO, we’re a small but mighty team on a mission to be the best and easiest way to learn at work.
We imagine a world where learning happens in the flow of work. Where employees maximize the minutes of their lives. Where knowledge is contextual, personalized and instantly accessible. Where learning at work is as easy and joyful as it is in our personal lives. This is the future we’re building at Spekit.
Our Product
Say goodbye to distracted zoom training sessions and lengthy LMS courses your teams will forget. Spekit is the leading just-in-time enablement platform that meets your reps when and where they need it, in the tools they use every day.
Spekit takes all of your training & enablement - for applications, processes, sales playbooks, SOPs and more and embeds that training directly in your employees’ tools & workflows. Think of Spekit as your employee’s digital sidekick that delivers real-time, personalized enablement in their flow of work™. Our unified enablement platform prioritizes three pillars: content, user experience, and flexibility. We focus on delivering the right answer, at the right time – all within a streamlined and intuitive interface. No more information overload, no more hunting for answers. That's Simple, yet Spektacular.
With over $60M in VC funding from Bonfire Ventures, Matchstick Ventures, The Foundry Group, Renegade Partners, The Operator Collective and other top VCs, thousands of employees from scaling startups to Fortune 400 organizations leverage Spekit to onboard new hires, facilitate change management and drive adoption of their tools and applications.
Location: Strongly preferred Denver, CO (2 days a week in office) or the surrounding Denver area. Open to remote US locations only within CA, IL, MA, MD, MI, NC, NM, NV, NY, OH, PA, TX, VT, WA, or WI, for candidates with specific industry-related experience. Must be willing and able to travel to Denver at least 4x per year, and onsite to customers as needed.
About the role
Our team is looking for a growth-minded, entrepreneurial Head of Sales with experience bringing new and innovative products to market and coaching teams to success. Reporting to our President & COO, Seth McGuire, the Director of Sales will build a winning sales strategy and inspire a team of highly driven and successful Mid-Market and Enterprise sales reps.
The right candidate will demonstrate an in-depth understanding of every facet of the sales organization, from metrics, reporting, forecasting, deal velocity, coaching, pipeline, and processes. They’ll be willing to get their hands dirty in deals, listen to calls and work closely with our reps to coach them through challenges.
The ideal candidate will demonstrate strength in leadership; they’re able to inspire and motivate others to reach their full potential, create a positive work environment where employees feel valued and engaged, can deliver meaningful feedback that creates a culture of accountability, and they understand how to develop effective strategies for achieving individual, team and company goals.
At Spekit, we have an extremely hard working, diverse, and supportive culture and we look for people who are curious and work to be a little better every single day. If you’re excited to pave the future of learning at work and want ownership over a large revenue generating piece of the business, we want to hear from you!

Some traits we’re looking for, from you:

  • You’re a proven sales leader; you have experience bringing new product(s) to market, creating an educational sales process to change the way customers think about how they run their business
  • You’re a storyteller at heart; you can turn new and complex ideas into simple, impactful narratives
  • You’re entrepreneurial in nature; you’re a strategic builder who can consistently execute but you aren’t afraid to roll up your sleeves and dive in to get things done
  • You lead by example; you can exemplify the grit, tenacity and empowerment that align with our core values and inspire our team
  • You take extreme ownership; you seize accountability and responsibility, you empower those around you and you find ways to solution challenges
  • You know how to recruit, onboard, develop and retain top sales talent
  • You’re data-driven; you know how to define and report on team KPIs and metrics, and use that to inform our sales strategy
  • You are able to cultivate internal relationships and influence cross-functionally across the business

In this role you’ll:

  • Build and scale a strategic and successful sales engine in close partnership with marketing and customer success teams, keeping the focus on our mission and vision
  • Coach and develop a diverse and high performing sales culture that inspires performance and achievement
  • Drive a scalable and repeatable sales motion that includes clarifying processes for each step of the sales funnel
  • Align the sales team on forecasting, SFDC discipline, pipeline management and QBRs
  • Support sales reps in their sales cycles, serving as an executive point of contact for prospects during their engagements during the sales cycle
  • Hire, onboard, mentor and develop sales reps, as well as future sales managers and directors
  • Motivate team members through creative incentives

You may be a fit if you have:

  • At least 6-8+ years of specific sales leadership experience with at least 5+ years at a B2B or B2B2C SaaS company
  • Reported directly to a C-Level (e.g. CEO, CRO) at an early stage company
  • Experience reporting quarterly sales metrics to executive teams and/or Board Members
  • Executive level presence with the maturity and strategic planning to implement complex, multi-threaded sales processes
  • Strong LinkedIn usage and presence for networking and also recruiting and prospecting
  • Knowledge and experience with sales and marketing tech stack including SFDC, Clari, Salesloft, LI Navigator, Chorus, Outreach, Hubspot and Zoom
We've got you covered!
- 100% paid employee Medical, Dental, Vision, and Basic & Optional Life Insurance. Benefits begin on your first day!
- Insurance coverage for the whole family, including flexible spending accounts
- Meaningful equity -- every employee is granted stock options when they walk in the door
- Flexible Paid Time Off (PTO) policy
- Hybrid work environment: Casual and open Denver, CO office with the ability to balance your time working from home
- 10 paid holidays days, sick leave, mental health days, and a 1-week end-of-year company shutdown
- Paid parental leave
- L&D stipend that can be used for learning opportunities at your discretion
- The chance to help build from the ground up. The hires we’re making now are foundational to our growth as a company!
Things we value, culture-wise:
Grit & Growth. We run towards challenges. If something seems unsolvable, it unleashes our persistence, our creativity, and our ability to move through uncertainty to create a solution.
Simple yet Spektacular. We’re in the early stages of building something really great and that requires a lot of hands on deck and a focus on execution. In this journey, we uncover joy in simplicity, obsess over the experience, pivot quickly and always reach for excellence.
Tenacity. The endless pursuit of customer love! We believe in collaboration, transparency, integrity, trust, listening, doing what is right, and always going above and beyond for our team and customers.
Belonging. We strive to build a company culture inclusive of all voices, differences of opinions, and the permission to be our authentic selves. We accept and celebrate what makes us unique and connects us to one another.
Enjoy the Journey. Love what you do and who you do it with! We embrace joy and kindness and we bring our authentic selves to work each day. We seek to share our optimism and compassion with everyone around us.
About the Team
At Spekit, we strive to be the change we seek. And the change we seek is a wealth of diversity in technology and the workplace. As a company with two female founders, we know that diverse and inclusive cultures drive innovative results. We’ve committed as an organization to elevate underrepresented minorities in technology through awareness, partnerships and even hosting our own scholarships to do our part in changing the status quo. If this sounds like the right place for you, we'd love to chat!