Senior Account Executive
Proper
Sales & Business Development
United States · Remote
USD 80k-90k / year + Equity
Posted 6+ months ago
Proper is a quickly growing startup that values your skills, voice, and happiness.
We’re a team of developers, designers, engineers, accountants, CPAs, project managers, and creatives from all over the world. But we’re also surfers, hikers, Sichuan-eaters, photographers, artists, world travelers, meme lovers, and life-havers.
Together, we provide the most technologically advanced property accounting services in the world - and we think that’s pretty epic. We’re proud to be creating something new that improves people’s lives while working together in a culture of collaboration, respect, communication, joy, and personal growth.
Read more about what we do at Proper.ai
We’re proud to create something new that improves people’s lives while working together in a culture of collaboration, respect, communication, joy, and personal growth.
We’re hiring a Senior Account Executive to own deals end-to-end — from first call to signed contract, selling Proper AI’s accounting and operations platform to leaders in property management and real estate.
This is a complex, consultative sale, not transactional. Our platform supports 39+ accounting and operational workflows, and buyers will ask detailed questions about how things work. You don’t need to be an accountant, but you do need to learn the business well enough to explain it clearly and confidently.
Many prospects are skeptical due to past experiences with outsourced accounting. Winning requires real discovery, trust-building, and operational fluency.
Proper is a San Francisco based tech startup. This position is remote but ideally based in Los Angeles.
Key Responsibilities
- Own deals from discovery through close
- Run consultative sales conversations with executive buyers
- Learn Proper AI’s workflows and explain how responsibilities are split between us and the customer
- Handle detailed operational questions
- Drive next steps and timelines
- Maintain clean, accurate CRM data and forecasts
- Contribute ideas to improve how we sell as we scale
Required Hard Skills
- 4–8 years closing experience in SaaS, tech-enabled services, or complex B2B sales
- Experience selling a multi-component or operationally complex product
- Comfortable selling to CEOs, CFOs, Controllers, or Owners
- Proven ability to run fast sales cycles (≈30 days) or compress longer ones
- At least 1 year using HubSpot
- Experience contributing to or improving sales process
- Education: Business, Finance, or Accounting background is a plus but not required. We weight cognitive aptitude and learning speed, assessed through a PI Cognitive Assessment, more heavily than a degree.
Required Soft Skills
- Fast learner who can explain complex things simply
- Strong listener who runs natural, two-way conversations
- Skilled at uncovering real pain, not just surface needs
- Comfortable handling curveballs in live conversations
- Knows how to create urgency without pressure
- Disciplined about process, forecasting, and follow-up
- Competitive and confident without being aggressive
Experience
- FinTech, Accounting Tech, Vertical SaaS, or Property Management SaaS
- Selling outsourced or tech-enabled services
- Startup or high-growth company background
- Familiarity with MEDDIC, Challenger, or SPICED
- Business, Finance, or Accounting education (nice to have, not required)
Salary + Benefits:
- Salary: 80,000 - 90,000USD/year + 100% variable compensation target with no cap on overperformance
- Benefits overview:
- 90% of the selected plan is covered for the employee
- 75% of the base plan is covered for each dependent
- Supplemental Accident, Critical Illness, Hospital Indemnity
- Employee FSA (Flexible Spending Account)
- Employee HSA (Health Savings Account)
- Employee Assistance Program (EAP)
- Coverage starts the 1st of the month following hire. See full benefit summaries and rates here
. Remote Work
. Utility allowance: monthly $30 USD (energy and internet)
. Furnishing allowance: one-time payment of up to $200 USD to furnish a home office
. Work equipment provided by Proper: computer, screen, and mouse
. 401K
. Health Insurance: Choose from 7 different plans:
Eligibility: Coverage begins on the 1st day of the month following your hire date
. Dental Insurance: Follows the same 90% employee / 75% dependent coverage structure
. Vision Insurance: 75% of the plan covered for the employee
. Life & AD&D Insurance: Employer-paid life insurance: 1x annual salary, up to $500,000
. Voluntary Guardian Life & AD&D: You may opt in or out
. Other Voluntary Benefits: You can choose to opt in to any of the following:
. Unlimited Paid Time Off (PTO): beginning two months after your start date. For sick, vacation, and personal days. We encourage a minimum of 12 days PTO each year. We observe all local holidays.
You can find a detail Benefits guide here
Proper is proud to be an equal opportunity employer committed to creating a diverse environment to work by offering the same opportunities to all applicants regardless of gender, sexual orientation, race, color, religion, disability, national origins, marital status, or other characteristics. We base our talent search exclusively on competencies, abilities and potential.
