VP Sales, North America

Job description

NOTE:  This is a 100% remote position, managing a distributed team, for candidates located in either EST or CST.

Cloud Academy is building the Operating System for Cloud and Tech Skills.

We combine software and content in a unique SaaS enterprise platform that allows large organizations worldwide to assess, develop and validate cloud and tech skills at scale. We solve two large problems for our customers: upskilling their workforce to let them build and design cloud and software solutions, and keeping their technical people up to date on everything related to cloud, software and data. We are a product company first and foremost, but over the years we have built a giant library of content that enables us to offer a unique set of solutions to deliver career paths, training and certifications at scale. We thrive on customization and data, so Cloud Academy enables Fortune 500 companies to fully customize their paths with our software and always have a clear snapshot of the tech skills they have, in real-time. Our team is global, with people in more than 10 countries worldwide. Our culture is American but our heart is European and we love to collaborate with our colleagues in all the other continents, from Australia to Asia.

Companies like Turner, Cognizant, SAS, and ThermoFisher customize Cloud Academy to contextualize learning and leverage the platform to assign, manage, and measure cloud enablement at scale. Learn more at cloudacademy.com.

We are looking for a VP of Sales for the North America territory (USA and Canada) to keep expanding our team and double down on our growth. Cloud Academy has been growing more than 100% YoY for the last few years in the Enterprise market, serving large companies that rely on our platform to assess, develop and validate their cloud and tech skills at scale.

We are building the Operating System for Tech skills, and we believe this will be a key component in the future of every large enterprise worldwide.

As the VP of Sales for North America you will be responsible for building, expanding and coaching our team of account executives, sales engineers and other operational roles on our team. The perfect candidate has been in several sales leadership roles before in the SaaS industry and has been growing sales teams from 20 to 100 people, managing communications, training, coaching and being an inspiration for the entire sales organization. We are looking for someone who has strong integrity and a great ambition to succeed and bring Cloud Academy toward $100M in yearly revenues in this territory.

Our next VP of Sales loves solving problems for large enterprise customers and loves to spend time building strong relationships with executives in these organizations, focusing on the creation of partnerships and investing in building a long-term relationship. Cloud Academy thrives on building programs at scale, being close to our customers, having weekly calls with them and understanding their problems and our product - this is a strong must for this position. Expect to own and drive a few large deals on your own, while driving the rest of the pipeline with your team.  Our preference is someone who has strong leadership skills, empathy, emotional intelligence and the ability to collaborate with our executive team at several levels. You must be passionate about coaching sales professionals, working with them, listening to their calls and working with them side by side to close deals, constantly inspiring them to overcome issues and grow them into better professionals. This implies having a strong data driven approach when it comes to pipeline, forecasting and structure of the team.

Cloud Academy is growing fast so, together with your team, you will spend most of your time looking for great sales leaders and professionals that can join us: we believe hiring is critical to succeed and we expect our next leader to be obsessed with it. You should spend 20% of your time hiring and researching candidates in the marketplace.

You will report to our CEO and founder and you should expect to spend much of your time working with him on strategy, team expansion and market expansions. You will also work closely with our VP of Marketing to ensure the marketing and sales organization is fully aligned with our revenue objectives.


  • Define and establish a more effective sales approach, methods, activities, benchmarks and expectations that will ensure building appropriate and accurate pipeline, close rate, and controlled sales cycle and basis for measuring performance of the sales team.
  • Implement robust performance measures and reviews using actual data versus benchmarks and expectations to drive strong sales execution.
  • Provide strong and credible leadership to the sales staff, setting a unified direction for the team and ensure priorities are clear at all times
  • A strong passion for our product and the ability to fully demo and discuss our software solution in the first 30 days, and keep improving that over time.
  • Successful track record in enterprise SaaS or software sales leadership going through rapid growth during the expansion phase.
  • Successful track record building, coaching, and managing a high performing, large inside sales team operating from remote offices.
  • Proven skills and strong inclination to build and manage forecasting properly for monthly and quarterly exit numbers with 90% precision. You will implement a strong forecasting method in the team and you will share that with the rest of the executive team.
  • Ability to get involved in complex scenarios and work directly with prospects and customers when needed.
  • Resourceful and able to work with whatever that is available.
  • Highly tech-savvy, with a BS or higher degree.
  • knowledge of Salesforce, Outreach, Gong and similar tools is a strong requirement for this position
  • Great knowledge of the cloud computing and tech space is a strong plus. You are familiar with AWS, Azure, Google Cloud, DevOps and other technologies that our customers use to scale their business every single day.
  • Strong passion for e-learning, education and people development is a must for this role and you should be excited about the problems you can solve deploying CA.
  • Tenacious - You bring a passion and desire to win against tough competition

You also possess these characteristics:

  • Trustworthy, reliable, accountable, respectful.
  • You have empathy, you love to spend time coaching people and improve them daily, no matter what they do and their level of seniority.
  • You lead by example: you are the best sales person in the team and you can quickly show that to the rest of the organization whenever it’s needed
  • Organized, planner, able to delegate without losing sight of the specifics.
  • High energy, data-driven, well read, articulate, curious, humble.
  • You thrive on feedback and you are coachable. You are well aware that this is the only way to grow and advance as an executive.


  • Competitive compensation and commission plan
  • Full benefits, including medical, dental, and vision
  • An exciting startup environment, working with an amazing product
  • Four weeks of paid vacation per year
  • Build your personal workstation