Head of Sales

About TruckSmarter

Logistics is one of the single largest industries in the world. Globally, logistics is an $8-$12 trillion dollar industry and in the US alone, ~$2 trillion, representing ~10% of GDP. A single percent of improvement drives profound change to every corner of the world—from the cost of our goods, to the livelihoods of local communities, to even the impact on our environment. To reshape the industry, at TruckSmarter, our focus is first on truck drivers. Trucks move 71% of freight in America (~$800bn annually) & the trucking industry represents nearly 6% of the full-time jobs in the country. If you look around you, every item has sat on a truck at one point on its journey to you. However, despite the industry being one of the greatest levers of innovation throughout history, it is still deeply fragmented & structurally misaligned. Our mission is to fix that—and we need your help.

The Role

This role is responsible for leading the Sales team for TruckSmarter’s growing factoring business. This role requires a dual skillset of sales and relationship-building skills, as well as experience hiring, developing and managing great talent. As the Head of Sales, you will be responsible for managing a team of 10 Account Executives and help them build a pipeline and drive net new customer acquisition strategies across the Factoring business - TruckSmarter’s largest business line.

You will report to the Head of Operations, one reporting level from the CEO. As such, you will be a key driver of the overall growth strategy, where you’ll work extensively with cross-functional teams to execute on growth and operational initiatives. You’ll be responsible for helping the team to build and manage pipeline, and will leverage this insight to forecast expected future revenue and identify additional areas of opportunity for growth.

We are not only looking for a sales professional who can coach and develop talent, hire and help to win business but also a strategic thought-leader who can drive forward winning strategies and processes to help exponentially grow the Factoring business. If you’re a motivated sales leader, invested in both building and growing people while also contributing to the growth of TruckSmarter’s fastest growing product set, this role is a great fit for you.

The following represents the expected range of compensation for this role:
• The annual OTE range for the target level for this role is $160,000-$180,000 (60/40 split) + equity + benefits (including medical, dental, vision, and 401(k))

Working model: TruckSmarter offers an in-office collaborative culture. This role is based out of our downtown Chicago office, and requires in-office presence three days per week (typically Mondays, Wednesdays, and Fridays).

What Excites You

• Lead and scale a growing team of Account Executives responsible for owning the end-to-end stages of the sales lifecycle from qualification through monetization

• Build, execute and manage pipeline strategies to drive conversion and maximize revenue

• Develop and implement strategies to build pipeline and accelerate our win rate. You will partner with operations, finance, legal, and product to build your strategy

• Identify, inform and implement sales process and enablement improvements in order to improve sales efficiency and drive optimal outcomes; track the impact of these projects and ongoing sales team performance

• Support the team as needed in sales and pipeline management, acting in an Account Executive capacity to identify prospects and help navigate them through the sales lifecycle

• Stay up-to-date on logistics industry trends, regulations, and best practices related to factoring and alternative financing solutions

• Coach and guide the team through new, ambiguous situations - helping to understand and resolve individual pain points while also creating larger-scale solutions and processes

• Provide ongoing coaching and training to the team, including active monitoring on key performance indicators

What Excites Us

• Bachelor's degree in business or a related field

• 10+ years of experience in sales or business development, preferably in the logistics or financial services industry

• 4+ years of people management experience attracting, developing, and motivating top talent, swiftly adapting and leading others through change, developing collaborative relationships with others, and leading and influencing a team

• Strong understanding of financial products and alternative financing solutions, inclusive of factoring and freight, a plus

• Experience using Salesforce to manage and track daily activities, including report building, Page/Field building and maintenance and basic integrations with other tools (ex: Slack, Outreach.io)

• Excellent communication and relationship-building skills

• Experience forecasting and managing your team, and aligning quota, to key performance metrics

• Experience in a sales operations / enablement capacity to identify and inform sales efficiency improvements

• Ability to multitask, prioritize, and react under pressure, navigating ambiguous situations

• Adaptability and ability to work well in a high-energy, high-paced team environment

• Proven track-record of building - you dream big and start small when it comes to business and people leadership and are an owner of sales strategy, job competencies, lead segmenting

What Success Looks Like

• Growth — Build and scale the Sales engine for TruckSmarter’s highest revenue-generating business line

• Ownership — Advocate for processes, products & strategies that you believe in and see them through to execution.

• Leadership — Lead a team of Enterprise Account Executives that attract new Factoring customers, while taking a people first approach to attract outstanding talent and support the personal development of members in your organization

• Build - You'll have your fingerprints all over TruckSmarter’s biggest business line

We Offer

• Health, Dental & Vision Plans

• Competitive Pay

• 401k

• Unlimited PTO

• Lunch + dinner in-office daily

• Commuter benefits

We would love to have you be a part of something special, and are excited to review your application.