A note on timing: we are pausing this search for a couple of months. Interviews start in late November 2026, we aim to make an offer in December, and the start date is January 2027. Exceptional candidates are welcome to apply now for fall and winter consideration.
👋 A note from Jesse, Head of Sales
Hi, I'm Jesse, Head of Sales at Maestra.
I've hired enough Account Executives to know this role isn't for everyone.
We're selling one of the most powerful ecommerce platforms on the market. Our customers replace multiple technologies with Maestra because they want a fundamentally better way to acquire, engage and retain customers.
That means our sales conversations are strategic. You're helping sophisticated ecommerce leaders rethink how they grow their business, not simply evaluating another software tool.
I'm looking for someone who has already proven they can sell complex software into ecommerce companies. Someone who enjoys becoming an expert, building trust with customers and winning deals because they create real value throughout the buying process - not because they're selling behind a well-known brand or a mature sales machine.
The people who thrive here are naturally curious, optimistic, resilient and genuinely excited about helping ecommerce brands grow.
If you're looking for a highly structured sales organization with rigid playbooks, dedicated Sales Engineers on every call and a top brand that opens doors for you, this probably isn't the right fit.
If you enjoy solving difficult customer problems, earning trust over time and helping build something exceptional, I'd love to meet you!
🔆 What you'll be selling
Maestra helps ecommerce brands replace multiple marketing technologies with one AI-powered platform. Our platform combines:
- Customer Data Platform (CDP)
- SMS
- Onsite Personalization
- Loyalty
- Analytics
- AI
...all in one platform and backed by a white-glove Customer Success team.
Every customer receives strategic implementation, ongoing Customer Success and a dedicated Slack channel with fast response times, giving you confidence that what you sell will be delivered exceptionally well after the customer comes on board.
Typical sales opportunities:
- $40,000-$300,000+ annual contract values
- Mid-market and enterprise ecommerce brands
- Multiple executive and technical stakeholders
- Competitive replacement opportunities
- Sales cycles that require thoughtful discovery, education and business case development
This isn't a transactional sale. Customers buy because they trust your understanding of their business and your ability to help them solve meaningful growth challenges. Success comes from deep discovery, understanding the customer's priorities, identifying compelling events and building a strong business case - not delivering the slickest product demo.
✍️ No annual contracts, a long-term view
Most SaaS companies require customers to sign annual agreements. Our customers remain with us because they continue receiving value every month, not because they're locked into a contract.
We're confident in the value we deliver and we don't believe in needing long-term contracts to keep customers. We believe that's how great partnerships work.
🤝 Relationship building is a competitive advantage here
Many of our customers don't buy immediately. Some evaluate us for months before they're ready to replace an existing platform.
That means one of the most important skills in this role isn't fast closing, it's nurturing.
The best Account Executives at Maestra know how to:
- Stay relevant over long sales cycles
- Teach instead of pitch
- Share useful ideas and industry knowledge
- Build trust without becoming pushy
- Follow up thoughtfully and consistently
- Become the first person customers think of when the timing is right
If your instinct is to push every opportunity toward a close, this isn't the right role.
👨🎨 What you'll do
- Own the full sales cycle from discovery through close
- Lead consultative conversations with ecommerce executives
- Build long-term relationships with prospects who may not purchase for months
- Understand compelling events and use them to create urgency at the right time
- Navigate complex buying committees and multi-thread opportunities
- Partner with founders, Customer Success and technical specialists on strategic opportunities
- Maintain disciplined forecasting and CRM hygiene
- Win competitive deals against larger, well-funded competitors
🤓 What we're looking for
Required
- 7+ years of B2B SaaS closing experience
- Proven success selling software into ecommerce companies
- Experience selling technically complex software involving multiple stakeholders
- A demonstrated history of consistently exceeding quota and performing among the strongest Account Executives on your team
- Experience selling competitive replacement opportunities
- Based in the United States or Canada
Nice to have
- Experience succeeding in an early-stage startup where ambiguity is normal
- Experience selling CDPs, ESPs, marketing automation, ecommerce infrastructure or adjacent technologies
- Experience working directly with founders or executive leadership
🔈 Interview process
During the interview process, I'll ask for specifics. Expect questions like:
- What annual quota did you carry?
- What percentage of quota did you achieve?
- Where did you rank relative to your peers?
- Which competitors did you consistently beat, and why?
- Why did the customer choose you?
- Tell me about a deal you patiently nurtured over many months before it closed.
Strong candidates usually enjoy these conversations because they have real stories backed by real numbers.
🫵 The kind of person who succeeds here
You:
- Already understand the ecommerce technology ecosystem (Shopify, ESPs, CDPs, SMS, retention marketing, personalization, etc.)
- Are naturally curious and genuinely enjoy learning how ecommerce businesses operate
- Stay composed under pressure and recover quickly from setbacks
- Seek direct feedback instead of avoiding it
- Can simplify complex technical concepts for executives
- Build credibility through expertise rather than polished sales tactics
- Sound like a trusted advisor, not a stereotypical salesperson
- Are resourceful and don't wait for someone else to solve problems for you
You probably won't enjoy this role if you:
- Need heavy enablement or rigid sales playbooks
- Prefer large, highly structured sales organizations
- Have only been successful selling for well-known brands with mature sales organizations, established enablement and strong inbound demand
- Prefer short, transactional sales over consultative relationship building
- Aren't excited by ambiguity, ownership and building something
🗓️ What you'll receive
- 12-15 qualified discovery meetings with ICPs every month
- A targeted enterprise account list
- AI-first sales tooling and enablement
- One of the strongest Customer Success teams in ecommerce SaaS
- Direct access to founders on strategic opportunities
- A remote-first culture with significant autonomy
💰 Compensation
We believe compensation should be transparent.
Our complete Account Executive compensation plan - including quota, commission structure and accelerators - is publicly available so every candidate understands exactly how the role works before interviewing.
View here: maestra.io/ae-comp
Compensation includes:
- $135,000-$160,000 USD base salary
- $270,000+ USD On-Target Earnings (OTE)
- Uncapped commission
- Stock options in a pre-Series A startup
- Comprehensive health benefits
- Remote-first
- Flexible PTO
Today, our sales team includes two full-time Senior Account Executives - one based in Texas and one in Europe. Our top-performing AE has earned $305,498.77 USD in total compensation between January and June 2026.
🎇 About Maestra
Maestra helps ecommerce brands replace multiple marketing technologies with one AI-powered platform for customer engagement.
We're founder-led and building for the long term. We care more about building an enduring company than chasing the next funding round.
If you're excited by technically sophisticated products, smart customers, long-term relationship building and the opportunity to become one of the best ecommerce software Account Executives in the industry, I'd love to hear from you.