Founding CTO - Lead CRM Development

Join to apply for the Founding CTO - Lead CRM Development role at The Sapling Group 2 days ago Be among the first 25 applicants Base pay range $70,000.00/yr - $100,000.00/yr Additional compensation types Annual Bonus Hiring Founding CTO - Nonprofit CRM Platform (Sapling) Comp: 70-100k Base salary + Equity available . Sapling is building a modern, systems-heavy CRM platform for nonprofits designed to handle fundraising, volunteers, contacts, donations, events, reporting, payments, and so much more in one unified product. We’re now funded and hiring a Founding CTO to own the technical foundation of the platform end-to-end. The CRM product and features are already fully designed. This role is focused on implementation, engineering execution, and scaling, not product ideation. This is not a simple donor database or lightweight SaaS. This is a mission-critical system that nonprofits rely on to run operations, move money, and generate reports and it requires serious technical ownership. What You’ll Own As Founding CTO, you will be the technical owner of Sapling’s nonprofit CRM. Implementing complex domain models (donors, organizations, funds, events, transactions, reports) Building and scaling payment infrastructure (Stripe, webhooks, subscriptions, failure handling) Implementing fundraising and donation workflows from existing product specifications Implementing automation systems (rules, triggers, async execution) Implementing role-based permissions across organizations and teams Building and maintaining third-party integrations (payments, email, accounting, exports) Ensuring data integrity, auditability, and reporting accuracy Making foundational decisions around system architecture and scalability Hiring and leading 1–2 senior engineers under you Working directly with founders on roadmap, tradeoffs, and execution You will write code. You will make architectural decisions. You will own the consequences. This Role Is For You If: ✔ You’ve built real B2B SaaS platforms used in production ✔ You’ve worked on CRM, ERP, fintech, or nonprofit / compliance-adjacent systems ✔ You understand payments beyond “Stripe Checkout” ✔ You’ve designed systems involving: financial transactions async workflows webhooks permissions and access control You think in systems, constraints, and long-term maintainability This Role Is NOT For You If: ✘ You’ve only built basic dashboards or CRUD apps ✘ You’ve never owned production payment or reporting systems ✘ You want tightly scoped tickets instead of ownership ✘ You avoid backend or data complexity Tech Environment (Flexible, But Serious) Modern frontend frameworks (React / Next.js) Backend systems (Node, Python, Go, etc.) #J-18808-Ljbffr

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...