Senior Account Executive – Mid Market

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 Senior 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. This position offers ambitious targets, a quick onboarding process, and rapid growth in both compensation and career advancement. Expect to see your efforts rewarded quickly and significantly as you help shape our success.

The ideal candidate will be a top performer with a proven track record of closing deals in the $30K-$100K range, consistently ranking in the top 10% of the sales team. This role focuses on mid-market accounts, requiring a proactive individual who can take initiative and drive results.

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

• 5 years of full-sales cycle B2B sales experience in the SaaS industry 
• Proven track record of achieving and exceeding sales targets, with experience closing deals in the $30K-$100K ACV range
• Proficient in sales methodologies such as Sandler, Challenger, MEDDIC, and others
• Exceptional communication, negotiation, and presentation skills, with the ability to build and maintain strong relationships with mid-market clients
• Highly motivated, hard-working, proactive, and able to take initiative to drive results
• Effective collaborator with internal teams while working remotely and autonomously
• Top producer in their current role, self-starter with a positive outlook and growth mindset
• A strong understanding of the marketing technology, e-commerce, online retail, and DTC brand landscape is highly preferred

Benefits

• Competitive salary and commission structure
• Employees may be able to purchase the company stock
• Comprehensive medical insurance (100% coverage for employees, 30% for dependents, vision and dental)
• Unlimited PTO
• 401k with 3% match
• Fully remote work and optional coworking space in Arlington, MA
• Opportunity to be part of an innovative and rapidly growing company
• Professional development and growth opportunities
• Work with a next-generation platform that sets the standard in marketing automation

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 20-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.