VP of Sales

Kaleidoscope is an early-stage B2B SaaS startup shaking up the scholarship and grant market. Our mission is to eliminate the financial barriers to advancement for millions of scholars across the world. We’re growing fast and looking for the right person to jump in as our VP of Sales to help us build and scale a high-performance sales team. If you’re someone who thrives in dynamic environments, loves building from the ground up, and is ready to make an impact, this could be your career-defining role.
As the head of sales, you will be responsible for driving new business by leading our BDR and sales teams, while owning and executing the go-to-market strategy. This is a hands-on role—you’ll be in the trenches with your team, providing coaching, strategizing, and stepping into key sales calls when needed. Your mission is to build a scalable sales engine that delivers results. In addition to sales, you’ll play a pivotal role on the executive team, contributing to strategic decisions and acting as the face of our brand in the market. This role goes beyond managing dashboards—you’ll focus on increasing deal sizes, improving conversion rates, and refining processes for sustainable success.
Key Responsibilities:

• Full sales responsibility and accountability. Includes partnering with CEO on building out G2M plan, working with executive team on executing it.
• Will be responsible to communicate plan and results to Board of Directors.
• Drive net new business revenue by leading a focused and motivated sales team.
• Increase average deal size and improve the efficiency of the sales process.
• Deliver accurate sales forecasts, establish measurable KPIs, and develop compensation and incentive plans to drive accountability and motivate the team.
• Create and execute a hiring plan to build a high-performing team that scales with the company with a structured onboarding process for new hires.
• Manage and continuously improve a strategic selling process for new and existing accounts, including forecasting, pipeline management, and sales execution.
• Partner with our Customer Success leader to drive upsell and cross-sell bookings, reducing churn and achieving customer revenue retention goals.
• Collaborate with Product leaders to identify, prioritize and act on new revenue growth opportunities.
• Build a seamless relationship with Marketing on sales positioning and lead generation.
• Act as a brand ambassador, representing Kaleidoscope at industry events, with key analysts, and as a spokesperson to elevate the company's position in the market.
• Work from our Minneapolis office at least 3 days per week.

Who You Are:

• Hands-On Growth Executive - You’ll jump into sales calls when needed, but you won’t carry a quota yourself. You’re in the weeds with your team, making sure every deal has what it takes to get across the line. You’ll also be asked to present to the Board of Directors and Investors.
• Startup & SaaS Experience - You’ve successfully scaled a SaaS sales team in a fast-moving startup environment.
• Talent Builder - You’ve developed a strong pipeline of talent, and you can tap into that network to help us grow our team.
• Strategic Planner - You can think beyond the next deal and plan for the future- designing sales strategies, forecasting needs, and preparing for long-term growth.
• All In - You understand the intensity of startup life and are ready to dedicate the time, focus, and energy required to succeed.

Sales Expertise:

• You’ve been a successful account executive, so you understand what it takes to close deals, manage deal velocity, and handle risk.
• Deep understanding of B2B SaaS sales models; experience designing and implementing sales models to decrease sales cycle time and increase win percentages.
• You set high standards for deal management, forecasting, and accuracy.
• You know the type of sales reps we need and how to manage different players- whether they’re A, B, or C players. You can make tough calls when necessary.
• You have experience designing commission plans, bonuses, and incentives that motivate and reward your team.
• You can jump in to support your team, whether it’s for strategy or tactical execution, and keep deals moving.
• You can represent the company’s growth plan and results to the board and investment community.

Fit for Kaleidoscope:

• You’re comfortable without a fully baked playbook and can handle the ups and downs of startup life.
• You understand the high-risk, high-reward nature of a startup our size and are excited by the challenge.
• You’re not afraid to be in the weeds, solving problems and pushing deals forward every day.

Industry Fit:

• You’ve sold B2B SaaS to SMB, Mid-Market, and Enterprise clients, and you understand how to manage multi-threaded deals.
• An understanding of higher education, non-profits, or the corporate giving space is a bonus but not required.
• You’ve got relationships you can tap into to help us with recruiting, sales, partnerships, or vendors.

Employee Benefits:

• A fast-paced and fun work environment in our North Loop Minneapolis office
• Competitive salary and stock options
• 401k program with match
• Full benefits package including medical, dental, vision, short-term disability, and basic-term life insurance
• Paid parental leave
• Flexible PTO program

Why Kaleidoscope?
Kaleidoscope is an early-stage company where you can make a real impact on both the business and the people we serve. This is your opportunity to help us build something meaningful and grow with a company that’s shaping the future of scholarship and grant management. If you’re ready to lead, innovate, and make a difference, we want to hear from you!
Equal Employment Opportunity
We’re proud to be an equal opportunity employer and welcome our employee’s differences, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, or Veteran status. Difference makes us better. Join us.