Sales & Sales Operations Lead

United States | Full-time | Fully remote


System Six, a modern, fast-growing and remote accounting and finance organization, is seeking an entrepreneurial sales professional to join us to build and scale our sales capabilities. As Sales & Sales Operations Lead, you’ll work directly with our CEO, participate in company leadership, and will both close new business and help design and build System Six’s long-term sales strategy and infrastructure.

System Six today serves our clients with bespoke, high-touch and high-value finance services ranging from bookkeeping to payroll processing to bill-pay to invoicing to everything in-between. Simply put, we serve as the front-line finance team for our clients, which range from small-businesses to nonprofits to wealthy families. We are fortunate to have consistently added new recurring revenue at a rate of 30%+ annually simply through referrals and word-of-mouth. We can’t wait for you to continue and accelerate that momentum through (1) managing our existing pipeline, (2) implementing sales infrastructure and (3) helping us select and execute on new verticals to target.    

Importantly, you’ll have the opportunity to grow significantly alongside System Six as we continue to grow over years and decades to come. Backed by a team from Stanford including a new CEO and highly-successful business-building investors who have built dozens of successful mid-sized companies, we seek to continue sustainable growth for decades to come and become a nine-figure business. We’ll grow organically, through acquisitions, and via additional lines of service offered to our customers. Success in these ambitions will require an expanded sales and marketing organization, and we hope you’ll build that team and capability underneath you in due time, eventually scaling to CRO.

Ultimately, our number one goal at System Six is to build the best place to work in remote accounting. We fundamentally believe our People are our Product, which means our team is always at the forefront of every decision we make. This intentionally creates a culture rooted in joy, flexibility and rewarding compensation. We certainly don’t get everything right - There’s Always Better - but we are excited to show you what we’re all about.

So What Are We Looking for In an Ideal Candidate?

  • Entrepreneurial spirit - You love building, are a self-starter, and love to run towards new challenges
  • Ability to close in a small-business environment - Whether you’ve sold accounting services, or other services to small organizations, you’ve always succeeded, and know how to navigate a relationship and consultative-based sales-cycle. You’ll spend a large part of you time managing our sales process, from responding to leads, holding Discovery calls, building proposals, closing clients, and various follow-up throughout
  • Love creating systems and processes - We’ve grown on the backs of internally-built sales systems, but we look forward to better leveraging sales-technology you’ll choose and implement to scale our sales capabilities. We’ll look to you to choose and implement a modern CRM such as Hubspot to improve our sales data, automate follow-up, etc. You’ll also implement important Customer Success workflows, such as quarterly check-ins, NPS surveys, referral outreach, etc.
  • Experience selecting and targeting new markets - While we can continue to grow 30%+ annually based of current inbound volume and enhanced referral volume, we also seek to select and go after new sales in several new target verticals in 2023. You will play a critical role in researching markets, desiging ICPs, and starting business development efforts in our newly selected markets 
  • Endlessly curious - You’ll talk to dozens of business owners and organizations monthly across a range of industries - possessing and showing genuine interest in a prospect’s organization, mission, and critical challenges is essential to building the trust and rapport necessary for success
  • Team player - You’ll work well with the accounting Team Leads to understand capacity, best match prospects to team members and jointly prepare prospect proposals 
  • Kind, Joyful and Trustworthy - We select team members that are a pleasure to work with - internally, and for our clients  

What Are Additional Benefits & Job Details? 

  • A joyful work environment where employees and culture are paramount - Our team loves what they do and loves System Six, and we can’t wait to show you how that energy permeates throughout our company 
  • A 100% remote environment - Work from where you choose and generally when you choose. We’ve been remote for 10+ years and are set up for you to succeed with the best technology and training available. We do expect you to attend quarterly company leadership meetings, our annual retreat, and important conferences throughout the year. 
  • Rewarding compensation - We strive to pay at the top of our industry, and will offer a competitive base and commission structure based on skill/experience (minimum $125,000 OTE+) with additional compensation including equity to be discussed
  • Competitive benefits - We provide health and dental insurance, retirement matching, PTO, maternity/paternity leave, bereavement and jury duty leave, annual wellness benefits, and annual in-person gatherings
  • Growth opportunities - We are a fast growing company on a multi-decade journey of evolution, and love team members who think with similar longevity. We relish promoting from within, and will support you in your efforts to further grow in sales leadership at System Six 

How to Apply

Apply online, and be sure to email a short paragraph explaining why you think you’ll be a great fit for this role and why you are excited to apply.

Also, be sure to tell us in the email that System Six’s favorite color is orange. This is an important test for detail we include in all our job applications!

System Six is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.