Let’s Roast.
What does it say about an organization when its VP of Sales role reads like a Wall Street boiler room job… but for nonprofits? This week, Jen and Paul dissect a job ad that demands $25M in new revenue, a 40-person team, and a compensation package so opaque it might as well be written in invisible ink. But the real womp-womp? The company’s mission is to make giving easier for charities. So why does this role feel like it’s designed to burn out its leader, and what does that mean for the causes they claim to serve? Buckle up: this roast is equal parts eye-opening and infuriating.
Follow along with the full job ad here:
The Bigger Picture
How do you design a high-stakes sales role for an organization whose mission is philanthropy, without turning it into a zero-sum game? This job ad exposes the tension between revenue growth and ethical responsibility, forcing us to ask:
Can capitalism and charity coexist in a single role? And if so, which thumb is on the scale?
At a Glance: The Job Profile
Job Title: Vice President, Enterprise Sales
Report-to Title: Unknown
Company Size: 201-500
Industry: Software Development — Fundraising Software
What do they do?: Donation platform helping nonprofits engage more supporters and grow revenue by providing easy ways to increase conversion, enable modern payment methods, and personalize the giving experience for every donor.
Head Office Location: Brooklyn, New York
Job Location: Remote (USA)
Geographical Operating Area: Global
Job Type: Full-Time / Permanent
For the Job Seekers
Did you come across a job ad like this? These questions might help you shed some light on what working there is really like:
What’s the real base salary? The ad only lists “on-target earnings”. How much of that is guaranteed, and how much is variable based on performance?
Who do you actually report to? No reporting structure is listed… how will you navigate authority and decision-making?
How will you manage 40+ direct reports? The ad mentions coaching and retention, but is that even possible without burning out?
What are the ethical guardrails? With revenue incentives this aggressive, how do you ensure alignment with the nonprofit’s mission?
What’s the turnover rate for sales positions on the team? If retention is a listed responsibility, what’s the history here? What are some of the historical challenges?
For the Job-Seeker Seekers
Are you writing a job ad for a similar role? Consider these hidden issues that might impact the success of your recruitment campaign:
Issues:
Lack of Transparency: Bundling compensation as “on-target earnings” without clarifying base salary is deceptive and could deter top talent.
Unrealistic Span of Control: Managing 40+ direct reports is unsustainable, expect high turnover or poor performance.
Ethical Misalignment: Aggressive revenue targets in a nonprofit context risk reputational damage and mission drift.
Authority Ambiguity: No clarity on reporting structure or decision-making power leaves the role powerless to enact change.
Fixes:
Restructure the Team: Break the 40+ reports into smaller units with clear leadership layers.
Clarify Compensation: List base salary, bonus structure, and equity (if applicable) upfront.
Define Ethical Guardrails: Explicitly outline how revenue goals align with the nonprofit’s mission.
Add Outcomes to the Job Ad: Specify what success looks like in 3, 6, and 12 months… not just revenue targets.
The Verdict
Jennifer Houle:
7.5 / 10 (Job Ad)
5 / 10 (Role Design)
The job ad was fairly well-written, though missing some important nuance for a VP-level role in a serious organization. The role design… worried me. This person is going to be constantly battling competing management priorities all while being compensated mostly based on revenue targets.
Paul Austin-Menear:
4 / 10 (Job Ad)
5 / 10 (Role Design)
It all sucked. The ethical conflict in the incentive structures were brutal. The job ad was missing honesty around earnings, and squished together a bunch of incompatible expectations. The role design… well, you might be able take your first week of vacation in around the year 2061. Like, come on.
Roast the Post is a passion project of Jen Houle and Paul Austin-Menear. The show helps job-seekers and employers get dud job ads out of their lives. We use contributions made on Buy Me a Coffee to help pay for our production costs, and donate anything raised beyond our costs to charity.
