Second Founding Account Executive - Upper Mid Market

About UsMaestra.io transforms marketing for e-commerce, online retail, and DTC brands with our next-generation AI-powered platform. As an Account Executive, youll 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 LOréal, KFC, Crocs, Panasonic, and Under Armour, our solution enables mid-size brands to boost revenue and reduce costs with a complete marketing strategy.Position OverviewWe seek a dynamic and results-driven Founding Account Executive to join our fast-growing team. This is not just any sales role; youll be a pivotal force in our US market expansion, working closely with our leadership to drive revenue and shape the future of Maestra.io. Were looking for a someone who loves building trust and relationships, enjoys long-term nurturing, and is focused on adding value in every interaction.We dont view our role as simply selling software; instead, we focus on building lifetime partnerships with our customers to help grow their business.Its not like we dont like closing"”we very much do. Its just that we want you to be focused on earning 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 ResponsibilitiesEducate and guide prospects through the buyer's journey to demonstrate how Maestra can drive their business growthIdentify, engage, and close new business opportunities within the mid-market segment, targeting the C-suite and VP/Director level marketing contactsDevelop and maintain a robust pipeline of prospects through strategic outreach, diligent management of provided leads, and relationship buildingPresent 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 plansNegotiate contracts and close deals efficiently, ensuring alignment with company goals and client expectationsConsistently meet and exceed sales targets, contributing to the overall growth and success of the companyContinuously develop and test new hypotheses to improve the sales process, refining marketing materials based on feedbackEffectively collaborate internally with founders, BDRs, heads of customer success and marketing, and other team membersHelp 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 for5+ years of full-sales cycle B2B sales experience in the SaaS industryProven track record of achieving and exceeding sales targets, with experience closing deals in the $60K-$150K ACV rangeProficient in sales methodologies such as Sandler, Challenger, MEDDIC, and othersExceptional communication, negotiation, and presentation skills, with the ability to build and maintain strong relationships with mid-market clientsHighly motivated, hard-working, proactive, and able to take initiative to drive resultsEffective collaborator with internal teams while working remotely and autonomouslyTop producer in their current role, self-starter with a positive outlook and growth mindsetA strong understanding of the marketing technology, e-commerce, online retail, and DTC brand landscape is highly preferredBenefitsCompetitive Salary & Commission: Attractive salary and commission structure.Equity Opportunity: Employees may have the option to purchase company stock.Comprehensive Medical Insurance: 100% coverage for employees, 30% for dependents, plus vision and dental.Unlimited PTO: Enjoy unlimited paid time off.401(k) with Match: 401(k) plan with a 3% company match.Direct Impact: Influence the value proposition and strategy (including your compensation plan).Advanced Revenue Operations: Leverage AI to automate HubSpot updates, meeting notes, follow-ups, and more.Team Collaboration: Work with top-tier CSMs who have 4x more time per customer compared to competitors.Flexible Work Environment: Fully remote work with an optional coworking space in Arlington, MA.Innovative & Rapid Growth: Be part of an innovative and rapidly growing company.Professional Development: Opportunities for continuous learning and career growth.Next-Generation Platform: Work with a cutting-edge platform that sets the standard in marketing automation.Finally, a Little More About Our CompanyAt 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, youll 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 youre a great fit. Important: Include the word Boston in the first sentence of your cover letter"”applications missing it won't be considered.

Created: 2025-02-11