April 27, 2022
Anywhere, United States of America
Job Type
Annual Salary: $90,000.00 - $100,000.00 - Bonuses above the base salary are paid out when targets are met.



At Direct, we provide lodging operators with a sleek, enterprise-grade software platform that's purpose-built for coordinating short-term rental operations, distribution, guest engagement, accounting, and third-party integrations. We have an awesome team and vision, great benefits, and a lot of room for growth!


We’re seeking analytical and high-energy operations professional to lead our growing Account Support (aka Customer Support) team here at Direct. Although this is a Director-level position, we still encourage ambitious individuals currently holding a lower title to apply, provided they have considerable experience in customer service, a proven track record of managing subordinates, and are motivated to move up the ladder (which would occur in the process of joining our Company).

At a high level, the Director of Account Support (“DAS”) is a knowledgeable, organized, outgoing, and technical operations leader who naturally possesses and expresses both strategic and tactical points of view. They think long-term, but also bring a sense of urgency. They mobilize resources to solve problems quickly, and they think outside of the box to ensure initiatives are executed on time. The teams they lead just get it done!

To that end, the Operations department at Direct includes both a proactive Customer Success ("CS") team primarily focused on helping customers reach their goals with our product, and a reactive Account Support ("AS") team primarily focused on helping customers resolve their issues with our product. The DAS is dedicated to the latter, responsible for not only overseeing and contributing to their subordinate's day-to-day efforts related to the AS issue lifecycle, but especially for spearheading the crafting, coordination, implementation, and ongoing maintenance of relevant core tools and systems, SOPs, and resources that will yield a high impact with customer retention and satisfaction (“major AS efforts”).

Alongside the Director of Customer Success (“DCS”), the DAS is a key contributor to the Company’s Operations department. Charting out major AS efforts, advising on when related tasks and subtasks need to be started and completed, and ultimately ensuring the efforts are carried out requires a true understanding of the product, process, and team inefficiencies and deficiencies. It is therefore critical the DAS demonstrates a willingness to roll up their sleeves and get into the trenches with their subordinates, draw insights and seek guidance from colleagues internally, and conduct independent research through online resources, meetups, industry peers, mentors, and more.

Reporting directly to the Chief Executive Officer, the DAS will aid in the Company’s strategic operational direction, help to drive innovation from an AS systems and process perspective, and work cross-functionally with members of the Product and Engineering teams in order to ensure the features we have available for use are in a stable, working state. This is a highly influential and impactful senior role where both collaboration and independence are essential to success. And, aside from the potential for future increases in base salary pay upon high performance, there is a path to a VP title if both the Company and the DAS are ready for it.


Benefits and Perks

  • Health Insurance: Get peace of mind with best in class medical insurance through Blue Cross Blue Shield, and dental and vision insurance through EMI Health
  • 401K: Save for retirement while lowering your taxable income by contributing on a pre-tax basis - smaller tax bite on your annual salary in the short-term, and extra security in the long run as your investments grow tax-free until you’re ready to retire
  • Paid Time Off: In addition to several planned and unplanned paid days off for holidays, we also provide 24 PTO days annually with an allotment to rollover unused days
  • Stock Options: Every team member at Direct has earned stock options, and if you work hard, you'll also have skin in the game as we work towards exciting goals


1. Leading the AS team

  • Ensuring SOPs are being followed by subordinates throughout all stages in the AS issue lifecycle, and holding them accountable
  • Actively participating in day-to-day efforts, and picking up the slack for subordinates whenever necessary
  • Leading standup meetings
  • Conducting performance evaluations
  • Fostering the Objectives and Key Results (OKR) program
  • Helping to further develop hiring and training processes

2. Spearheading major AS efforts

  • Evaluating, further developing, setting up, implementing, and maintaining SOPs, as well as relevant core tools, systems, and resources, either independently, or by delegating to subordinates when appropriate
  • Taking the lead with damage control, which involves intervening in communications with high-value customers deemed at risk of churn, and working closely with the VP of Product to qualify, log, triage, and resolve the highest priority issues

3. Tracking AS team KPIs

  • Leveraging core tools and systems to track KPIs related to AS tactical and strategic efforts, team and team member performance, and active and inactive customers
  • Being an active participant, and reporting KPIs too, the Leadership Council



  • Proven experience in Account/Customer Support, or role in relevant department
  • Proven experience working in travel/hospitality technology, preferably short-term rental property management software
  • 5+ years of experience using enterprise software with an emphasis on web applications and B2B SaaS
  • Excellent people skills, business acumen, and exemplary work ethics
  • 3+ years of technical leadership (overseeing 3+ people)
  • Working knowledge of data analysis and performance/operation metrics
  • Working knowledge of Google Suite, Intercom, Slack, Stripe (Jira, Confluence, Asana,, a plus)
  • Outstanding organizational and leadership abilities
  • Aptitude in decision-making and problem-solving
  • Ability to deliver best-in-class service to customers
  • Experience designing, building, and executing scalable processes
  • In-depth knowledge of operations and hands-on experience implementing and utilizing actionable metrics and KPIs to improve operational efficiency
  • Hands-on experience with process and workflow principles and practices
  • Demonstrated track record of successfully hiring, managing, coaching, and retaining team members
  • Experience dealing with competing priorities in a fast-paced environment


Annual Salary: $90,000.00 - $100,000.00

Bonus Details: Bonuses above the base salary are paid out when targets are met.


  • Paid time off such as PTO, sick days, and vacation days
  • Health insurance
  • Dental insurance
  • Vision insurance
  • Retirement benefits or accounts