Penn Foster
Head of Sales (VP)
Penn Foster, San Francisco, California, United States, 94199
The trucking industry is the backbone of the global economy. Roughly 80% of what we consume in the U.S. is moved by trucks. Those trucks are powered by over 3.5 million drivers per year and create over $700B in annual revenue. Trucking is a massive industry but it is a traditional industry and like many traditional industries, it is ripe for disruption.All industries of this scale have major corporations involved, and this is true of trucking as well, but it’s unique in that the drivers powering these trucks are truly the hearts and souls of the industry. Over the last couple of years, we have seen an entry of new technology into the space, and some high-profile tech companies like Uber Freight and Convoy have paved the way. These companies have really focused on logistics and route optimization, on serving the enterprises in trucking, the brokerages, versus the individual drivers. These millions of drivers that make up the backbone of the American economy have largely been overlooked.CloudTrucks is the first platform specifically designed to empower the driver.CloudTrucks optimizes operations and accelerates cash-flow for drivers, so they can focus on building their businesses. CloudTrucks has built a mobile app where drivers can see loads coming from many different shippers across the country, and an algorithm (called Schedule Optimizer) which helps drivers make better decisions on which loads to take to increase their revenue.From instant payments to smart load scheduling and competitive rates, CloudTrucks empowers independent Owner-Operators to make the most of every run. And they fit perfectly into the existing trucking software ecosystem.Role and Responsibility:
CloudTrucks is looking for a seasoned and experienced sales leader to propel them to the next level. The Head of Sales will work closely with CloudTrucks’ management team to shape the company’s commercial strategy. They will lead the execution of this strategy, drive revenue, and build an organization that is capable of operating at scale. In this role, you will be involved and own all aspects of the sales cycle.This is a fantastic opportunity with a company that has a huge (and growing) market; strong product-market fit due to an early lead and strong founding team. As an integral member of the organization, you will play a key role in CloudTrucks’ success.The Head of Sales will report to Tobenna Arodiogbu, CEO and Co-founder.Key Deliverables:
Own the numbers. Understand CloudTrucks’ current customer traction and path to market. Leverage this knowledge to build a playbook and drive a clear go-to-market strategy.Drive growth; plan the expansion strategy and scale the revenue function.Come in with a strong understanding of the buyer, our customers. Resonate with the unique challenge the CloudTrucks platform is solving. Be the voice of the customer and ultimately help shape product development and longer-term company strategy.Develop differentiation in the market based on a thorough understanding of the needs of the customers and the competitive landscape.Integrate the sales perspective into the fabric of the company.Cultivate and build working relationships between stakeholders across the company.Partner closely with Marketing to understand, strategize and create a strong leads funnel.Build a sales team. You will be responsible for working with recruiting and growing the team based on the organization’s needs. You have a deep understanding of what makes a successful teammate at all levels of careers and how that plays into the overall sales function.Design inspiring quota framework and compensation plans that are fair and also continue to motivate the team. Build a scalable process around pipeline, strategy, team configuration, compensation, etc.Hire great people and set clear expectations to create a culture of accountability and excellence. Train, mentor, and lead the team to the highest levels of performance possible.Map out the sales infrastructure and set expectations and goals for the team.Bring in operational rigor around overall effectiveness of pipeline management, process, methodology, metrics, review, cadence, tools.Drive an experimentation culture and environment across the revenue team.Requirements:
Proven experience being a VP of Sales or similar role at a technology company. Owning the revenue organization and strategy.A career defined by progressively expanding sales leadership roles.Experience selling to a Small Business audience with a high velocity motion is critical.Has owned and built sales infrastructure, training, and operations at a high-growth company.We are looking for a highly-analytical sales leader to lead in data-driven decisions.Experience taking new products to market.Personally active with customers and partners; adept at both closing deals and leveraging those relationships to expand footprint and continue to grow.Great storytelling ability - can map new products to customer value in a compelling way.Builder; “player-coach” mentality with a strong track record in fast-moving environments.We are looking for someone collaborative to work closely with marketing, customer success, and the rest of the GTM organization.Success as a leader and manager. Strength in hiring great people; has built high-performing teams and comes with a network that can be leveraged. Great talent scout and coach.Highly disciplined and organized, both operationally and in thought process.We are looking for someone who is excited about this space; there is a strong level of passion and buy-in around CloudTrucks’ mission.Preferred Experience:
Experience leading sales at a marketplace company.Experience working in freight tech.About CloudTrucks
CloudTrucks is a virtual trucking carrier in the multi-billion dollar trucking space. Core to this industry are over 3.5M truck drivers. They move more than 70% of all goods transported around the U.S., yet operate in a highly fragmented industry with huge opportunities for products, services, and automation. We strive to deliver solutions that help truck drivers operate with much greater efficiency, increase their revenue, and offload business complexity. We are looking for uniquely exceptional people to join us on our journey as we massively scale into an industry-defining business.We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.Compensation Range: $175K - $200K
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CloudTrucks is looking for a seasoned and experienced sales leader to propel them to the next level. The Head of Sales will work closely with CloudTrucks’ management team to shape the company’s commercial strategy. They will lead the execution of this strategy, drive revenue, and build an organization that is capable of operating at scale. In this role, you will be involved and own all aspects of the sales cycle.This is a fantastic opportunity with a company that has a huge (and growing) market; strong product-market fit due to an early lead and strong founding team. As an integral member of the organization, you will play a key role in CloudTrucks’ success.The Head of Sales will report to Tobenna Arodiogbu, CEO and Co-founder.Key Deliverables:
Own the numbers. Understand CloudTrucks’ current customer traction and path to market. Leverage this knowledge to build a playbook and drive a clear go-to-market strategy.Drive growth; plan the expansion strategy and scale the revenue function.Come in with a strong understanding of the buyer, our customers. Resonate with the unique challenge the CloudTrucks platform is solving. Be the voice of the customer and ultimately help shape product development and longer-term company strategy.Develop differentiation in the market based on a thorough understanding of the needs of the customers and the competitive landscape.Integrate the sales perspective into the fabric of the company.Cultivate and build working relationships between stakeholders across the company.Partner closely with Marketing to understand, strategize and create a strong leads funnel.Build a sales team. You will be responsible for working with recruiting and growing the team based on the organization’s needs. You have a deep understanding of what makes a successful teammate at all levels of careers and how that plays into the overall sales function.Design inspiring quota framework and compensation plans that are fair and also continue to motivate the team. Build a scalable process around pipeline, strategy, team configuration, compensation, etc.Hire great people and set clear expectations to create a culture of accountability and excellence. Train, mentor, and lead the team to the highest levels of performance possible.Map out the sales infrastructure and set expectations and goals for the team.Bring in operational rigor around overall effectiveness of pipeline management, process, methodology, metrics, review, cadence, tools.Drive an experimentation culture and environment across the revenue team.Requirements:
Proven experience being a VP of Sales or similar role at a technology company. Owning the revenue organization and strategy.A career defined by progressively expanding sales leadership roles.Experience selling to a Small Business audience with a high velocity motion is critical.Has owned and built sales infrastructure, training, and operations at a high-growth company.We are looking for a highly-analytical sales leader to lead in data-driven decisions.Experience taking new products to market.Personally active with customers and partners; adept at both closing deals and leveraging those relationships to expand footprint and continue to grow.Great storytelling ability - can map new products to customer value in a compelling way.Builder; “player-coach” mentality with a strong track record in fast-moving environments.We are looking for someone collaborative to work closely with marketing, customer success, and the rest of the GTM organization.Success as a leader and manager. Strength in hiring great people; has built high-performing teams and comes with a network that can be leveraged. Great talent scout and coach.Highly disciplined and organized, both operationally and in thought process.We are looking for someone who is excited about this space; there is a strong level of passion and buy-in around CloudTrucks’ mission.Preferred Experience:
Experience leading sales at a marketplace company.Experience working in freight tech.About CloudTrucks
CloudTrucks is a virtual trucking carrier in the multi-billion dollar trucking space. Core to this industry are over 3.5M truck drivers. They move more than 70% of all goods transported around the U.S., yet operate in a highly fragmented industry with huge opportunities for products, services, and automation. We strive to deliver solutions that help truck drivers operate with much greater efficiency, increase their revenue, and offload business complexity. We are looking for uniquely exceptional people to join us on our journey as we massively scale into an industry-defining business.We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.Compensation Range: $175K - $200K
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