Senior Account Executive
WFA Digital Insight
Flex is positioning its Senior Account Executive to own the full revenue cycle in a niche that blends fintech and proptech. The role isn’t just about hitting quotas; it requires navigating complex, multi‑stakeholder deals with property managers and C‑level executives while coordinating closely with product, marketing, and customer success. What sets this opening apart is the explicit focus on mid‑market accounts within the rental sector, meaning candidates will balance high‑velocity prospecting with deep, strategic relationship building. Flex’s remote‑first culture adds a layer of autonomy, but success will hinge on disciplined pipeline management in Salesforce and the ability to translate data into actionable sales tactics.
Job Description
Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?
About the role
As a Senior Account Executive at Flex, you will play a critical role in driving revenue growth and expanding our presence within the rental real estate sector. This position is responsible for engaging and closing high-value mid-market accounts, developing long-term strategic partnerships, and working closely with cross-functional teams to ensure customer success. The ideal candidate has a strong background in mid-market or enterprise sales, a history of exceeding revenue targets, and experience managing complex sales cycles with executive stakeholders.
What you’ll do
- Identify, target, and engage key large accounts within the rental real estate industry to drive revenue growth.
- Own the entire sales cycle, from prospecting and initial outreach to negotiation, closing, and contract execution.
- Build and maintain relationships with C-level executives, property management firms, and key decision-makers.
- Conduct high-impact sales presentations and product demonstrations to showcase the value of Flex’s solutions.
- Collaborate with Marketing, Product, and Customer Success teams to ensure a seamless sales process and client onboarding.
- Manage a strategic sales pipeline, utilizing CRM tools to track progress and accurately forecast revenue.
- Develop and execute account-specific sales strategies to maximize adoption and engagement.
- Consistently exceed sales quotas and revenue targets.
Key qualifications
- 6+ years of enterprise sales experience, preferably in FinTech, PropTech, or SaaS industries.
- Proven track record of consistently exceeding quotas and driving substantial revenue growth.
- Strong ability to build and nurture executive-level relationships within mid-market and enterprise accounts.
- Excellent communication, presentation, and negotiation skills.
- Ability to navigate complex sales cycles and manage multiple stakeholders.
- High level of initiative, self-motivation, and the ability to thrive in a fast-paced, dynamic environment.
- Experience leveraging various outbound prospecting channels, including phone, email, and social media.
- Proficiency with CRM tools (e.g., Salesforce) and data-driven sales methodologies.
Compensation
The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. This is a commission earning role. The OTE (On Target Earnings) listed below:
Life at Flex
We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.
Offices
Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.
Benefits
For full-time U.S. employees we offer:
- Competitive medical, dental, and vision
- Company equity
- 401(k) plan with company match
- Unlimited paid time off + 13 company paid holidays
- Parental leave
- Free Flex subscription
For full-time non-U.S. employees, we offer:
- Competitive compensation + company equity
- Unlimited PTO
How to Stand Out
- Highlight concrete examples of mid‑market or enterprise deals you closed, especially those involving SaaS or fintech products.
- Prepare a short case study that shows how you used Salesforce to manage a complex pipeline and improve forecasting accuracy.
- Practice delivering a 5‑minute demo that focuses on Flex’s rent‑payment flexibility and ROI for property managers.
- Emphasize any experience working with C‑level executives; be ready to discuss how you built those relationships.
- Research Flex’s product basics beforehand and weave that knowledge into interview answers to demonstrate genuine interest.
- When negotiating, reference the OTE range provided and be prepared to discuss performance‑based commission structures.
- Watch for signs that the interview team values data‑driven decision making; bring metrics from past roles to illustrate your analytical approach.
This is a remote position listed on WFA Digital, the platform for professionals who work from anywhere. Browse more remote jobs across all categories.