System Six is a fast-growing, 100% remote organization delivering full-cycle accounting, tax, and other professional services to hundreds of clients nationwide. We have grown over 300% to $8M in revenue the last 5 years, and are thrilled to now be a team of nearly 70 strong. We work Relentlessly every day to build the best place to work in remote professional services - a place where team are Empowered and Elevated and clients are consistently Wow’ed. As we prepare for the next exciting stage of our growth, we are seeking an ambitious, talented and joyful Head of Sales and Business Development to close healthy existing lead flow and drive further growth.
The Head of Sales and Business Development's (HOS) responsibility will be two fold. First, they will continue to own and scale existing inbound, which today yields 20-30 Discovery calls and ~$500K closed ARR per quarter across our three segments, Core accounting services (for $1-$10M revenue businesses), Enterprise accounting services (for $10-$50M revenue businesses), and Tax. Next, the HOS will lead new business development efforts for System Six in the Family Office, Independent Sponsor and Lower-Middle Market PE ecosystem, working closely with CEO Chris Williams to leverage his PE background to further sell into investor backed businesses. Along the way, this leader will help continuously professionalize the sales function at System Six and collaborate more broadly with the entire leadership team, playing a pivotal role in System Six’s continued and sustained growth.
This is a fantastic full time, U.S. based position affording someone the opportunity to grow a sales department inside an ambitious yet balanced organization. System Six is backed by a small group of seasoned, long-term oriented small business investors and we are on a multi-decade journey to build a thriving, one-stop shop for recurring professional services. We can’t wait for you to join us.
So what are we looking for in an ideal candidate?
Personal Skills
- Adaptable communication skills externally with prospective clients who have diverse business and financial backgrounds - simple when needed; deep and sophisticated when valuable
- Excellent communication skills internally across a variety of channels; this is a collaborative sales environment where you scope closely with Delivery teams on every opportunity
- Speed and resourcefulness. An independent problem solver that can also ask for help when needed
- Humility, patience, and a deeply rooted servant leadership mentality
- Joy. A pleasure to work with; energetic and warm. You are enthusiastic about work daily
Professional Skills
- 7+ years of proven success in sales and business development in a consultative, professional services sales environment, preferably in accounting
- Track record of hitting goals selling to and building relationships with SMBs, larger Lower Middle Market (LMM) businesses, and their various advisors, investors and other 3rd parties. This network will follow them to System Six
- 3+ years of leadership or management experience overseeing a sales team, including hiring and coaching other team members
- Fluency with Hubspot and other critical sales tools. Experience managing campaigns, pipelines and tracking sales performance metrics within a CRM system
- Strategic thinking. Ability to work with the executive team to align sales strategy with company-wide growth goals and long-term vision
- Strong familiarity with how financial operations support small to midsized businesses
- Bachelor’s degree in business, marketing, finance, or a related field preferred
As our Head of Sales and Business Development, you’ll own the full client journey, from first conversation through signed engagement, all while laying the groundwork for a scalable sales function as we grow. Your primary responsibilities are:
- Lead and own the sales process - You will run discovery calls, collaborate with Delivery teams in scoping, pricing and client fit, send and close proposals, all while maintaining or improving our current close rates across current channels. Post close, you’ll remain engaged, ensuring clients transition into delivery with clear internal and external expectations
- Increase growth through strategic business development - You will rely on a combination of your network, our existing clients and partners, and future clients and partners to ultimately increase our growth among $10M+ revenue businesses. You’ll attend conferences, travel, and do whatever is necessary to effectively expand into new channels
- Manage and improve sales data - Enhancing tracking all opportunities in our CRM (Hubspot), ensuring timely follow-up, accurate forecasts, and healthy data hygiene.
- Build the foundation for a future sales team - While this role will initially function as an individual sales leader, you will also begin laying the groundwork for a scalable sales function by documenting processes, refining messaging, and identifying key metrics.
- Contribute to the strategic growth of System Six - You will work closely with the CEO as part of the leadership team to align sales efforts with company-wide growth goals.
Importantly, here’s what’s in it for you:
- A joyful work environment where employees and culture are paramount. We understand that we are all human and we want your success in your professional life to Elevate and Empower your personal life
- A 100% remote environment. We've been remote for 10+ years and are set up for you to succeed remotely while working with flexibility during daytime professional hours
- Strong compensation. This exempt position offers a base salary range of $100,000-$150,000+ depending on experience plus a meaningful, uncapped variable component tied directly to closed ARR. OTE of $200,0000-$300,000+ year 1, expect to ramp beyond.
- Competitive benefits. We provide all of your work equipment, health, vision and dental insurance, 401k matching, PTO, family leave, annual in-person gatherings and many other leading benefits
- Growth opportunities. We are a steadily growing company on a multi-decade journey of evolution. We relish promoting from within, and will support you in your efforts to grow with System Six
Excited to apply? Here’s how!
Apply online via the link and let us know our favorite color is orange.
At System Six, we truly believe in the importance of maintaining a healthy work-life balance and we understand the importance of family and personal commitments. While we encourage our employees to prioritize their well-being outside of work, we do not allow team members to take on additional paid accounting or bookkeeping tasks beyond their role with us. This is a 100% remote, work from home role with travel required 4-6 times a year.
System Six is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We encourage all backgrounds to apply, and prohibit discrimination of any kind based on any and all protected classes.
