Senior Account Executive – Mid Market

Maestra; Boston (MA); Remote; USD 250,000 - 300,000; Full time

Job summary

Join a fast-growing company revolutionizing marketing for e-commerce brands! As a Founding Account Executive, you will play a key role in expanding Maestra's presence in the US market. With a focus on building lasting partnerships, you will guide clients through their journey, demonstrating how our innovative AI-powered platform enhances customer experiences and boosts revenue. This is an exciting opportunity for a top-performing sales professional to make a significant impact in a dynamic environment, while enjoying competitive compensation and comprehensive benefits. If you are ready to drive results and thrive in a collaborative culture, this role is for you.

Benefits

Unlimited PTO

Comprehensive Medical Insurance

401(k) with Match

Equity Opportunity

Flexible Work Environment

Professional Development

Team Collaboration

Direct Impact

Qualifications

• 5+ years of full-cycle B2B sales in SaaS with a proven track record.
• Exceptional communication and negotiation skills are essential.

Responsibilities

• Educate prospects on how Maestra can drive business growth.
• Identify and close new business opportunities in mid-market.

Skills

B2B sales experience

Sales methodologies (Sandler, Challenger, MEDDIC)

Communication skills

Negotiation skills

Presentation skills

Relationship building

Proactive mindset

Tools

HubSpot

Job description

Second Founding Account Executive – Upper Mid Market

This range is provided by Maestra. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$250,000.00/yr - $300,000.00/yr

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 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 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 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 $60K-$150K 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

Competitive 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 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.

Seniority level

Mid-Senior level

Employment type

Full-time

Job function

Sales and Business Development

Industries

Technology, Information and Internet