What are the responsibilities and job description for the Second Founding Account Executive – Upper Mid Market position at Maestra?
About Us
Maestra.io transforms marketing for e-commerce, online retail, and DTC brands with our next-generation AI-powered platform. As an Account Executive, you'll help brands improve customer journeys and campaign conversions. Our unified real-time platform manages loyalty, website personalization, and all customer communications, beyond email and SMS automation. Trusted by brands like L'Oréal, KFC, Crocs, Panasonic, and Under Armour, our solution enables mid-size brands to boost revenue and reduce costs with a complete marketing strategy.
Position Overview
We seek a dynamic and results-driven Founding Account Executive to join our fast-growing team. This is not just any sales role; you'll be a pivotal force in our US market expansion, working closely with our leadership to drive revenue and shape the future of Maestra.io.
We're looking for a someone who loves building trust and relationships, enjoys long-term nurturing , and is focused on adding value in every interaction.
We don't view our role as simply selling software; instead, we focus on building lifetime partnerships with our customers to help grow their business.
It's not like we don't like closing—we very much do. It's just that we want you to be focused on e arning between $500k and $1M in 2-4 years instead of squeezing short-term gains.
The ideal candidate will be a top performer with a proven track record of closing deals in the $60K-$150K range , consistently ranking in the top 10% of the sales team .
Key Responsibilities
- Educate and guide prospects through the buyer’s journey to demonstrate how Maestra can drive their business growth
- Identify, engage, and close new business opportunities within the mid-market segment, targeting the C-suite and VP / Director level marketing contacts
- Develop and maintain a robust pipeline of prospects through strategic outreach, diligent management of provided leads, and relationship building
- Present and demonstrate the value of Maestra.io’s solutions to potential clients, tailoring pitches to meet their specific needs, and developing business cases and mutual action plans
- Negotiate contracts and close deals efficiently, ensuring alignment with company goals and client expectations
- Consistently meet and exceed sales targets, contributing to the overall growth and success of the company
- Continuously develop and test new hypotheses to improve the sales process, refining marketing materials based on feedback
- Effectively collaborate internally with founders, BDRs, heads of customer success and marketing, and other team members
- Help onboard future Account Executives by providing guidance and support to ensure they are well-integrated and equipped to succeed in their roles.
Who we are looking for
Benefits
Finally, a Little More About Our Company
At Maestra, our mission is to empower marketers to drive business growth by improving how customers interact with their brand at every step. We are a fast-growing 30-person spin-off from a highly successful European business, leveraging cutting-edge marketing technology and a proven business model.
Our unique self-management culture emphasizes transparency, empowerment, and integrity, with transparent P&L, open and self-set salaries, honest sales practices, consent-based decision making, and minimal management.
With founders in Boston and a significant part of our team in the Netherlands, you'll be one of our early US employees, playing a pivotal role in our US expansion.
Are you a top-performing sales professional ready to make an impact? Maestra.io is looking for someone like you! Submit your resume and a cover letter explaining your relevant experience and why you're a great fit. Important : Include the word Boston in the first sentence of your cover letter—applications missing it won’t be considered.
Salary : $60,000 - $150,000
