Sales Jobs in Everett, MA

Enterprise Account Executive

(Enterprise SaaS | Secure Collaboration | Cloud-Native Platform)

The Company

A well-established, cash-flow positive software company founded over a decade ago, with a tight-knit team of approximately 50 employees. The business has seen meaningful acceleration in demand following shifts in how enterprises approach secure collaboration and remote work.

The Product

A secure file sharing and collaboration platform designed for enterprise environments. The solution differentiates itself by layering directly on top of existing Microsoft 365 or Google environments, allowing organizations to maintain full control of their data—files never leave the customer’s infrastructure.

The platform uses intelligent, policy-driven security to dynamically determine how files can be accessed based on user identity, file sensitivity, and risk level. This makes it especially compelling for organizations operating in highly regulated industries with strict security and compliance requirements.

The Role

This is a new logo-focused Enterprise Account Executive role targeting large, complex organizations.

• Focus on enterprise-level accounts, primarily companies with 1,000+ employees
• Own the full sales cycle from prospecting through close and expansion
• Approximately 70% self-sourced pipeline today, with 30% supported by BDRs and marketing (goal is to move to a 50/50 split)
• Deals are predominantly land-and-expand, with significant long-term account growth potential
• Engage with buying teams such as Digital Workplace, IT, and Security within target organizations

Sales Details

• Quota: $1M–$1.5M annually
• Deal Sizes: $70K minimum, up to $1M+
• Sales Cycles: 4–9 months
• Customers: Large, well-known enterprise brands across multiple industries

Ideal Background

• Experience selling AI-powered or cloud-native technology
• Proven success managing complex enterprise sales cycles involving multiple stakeholders and departments
• Background selling into highly regulated industries such as healthcare, insurance, or financial services
• Comfortable operating in a technical sales environment

Must-Haves

• Experience selling into organizations with 1,000+ employees
• Strong technical acumen and ability to sell sophisticated solutions
• True hunter mentality with a track record of building pipeline and closing net-new business

Compensation

• Base Salary: $140K–$160K (DOE)
• On-Target Earnings: $300K–$320K
• Uncapped commission plan

Rails, a global contemporary lifestyle brand, is looking to hire part-time Sales Associates for its retail store in Boston.

Key Responsibilities:

• Deliver an outstanding customer experience. Curate the experience for the customer, walking them through the RAILS story
• Develop and maintain long lasting client relationships by establishing a return client base
• Maintain an accurate, efficient, and effective client book
• Ensure image and grooming standards are professional and reflective of RAILS brand
• Maintain visual merchandising standards daily
• Consistently achieve personal and overall store sales goals
• Maintain an active floor presence
• Assist with organization and upkeep of both the front and back of house
• Additional responsibilities as required

Requirements:

• Passion for customer service, styling, and product
• Flexible availability, including weekends and holidays
• Results driven
• Team player
• Strong time management and communication skills
• Ability to manage multiple and competing work priorities, demands, and changes
• Experience in a retail sales environment, preferably in contemporary apparel, preferred

Founded in 2008 by Los Angeles native Jeff Abrams, Rails has grown from a small label - started with just a single hat - into a full collection of women’s and men’s apparel. Sold at top international retailers and worn by a loyal following of celebrities and tastemakers, the brand has come to define a new classic heritage and relaxed sensibility. Rails is sold in 30 countries by more than 1000 retailers, including its own flagship stores in New York, San Francisco, Newport Beach, Paris, London and Amsterdam.

Summary:

This individual is fashion obsessed and client and brand centric with all efforts. With the goal of supporting client needs through styling efforts, this individual is a passionate brand ambassador who is responsible for promoting brand engagement with clients, partners and within their city. This role will act as a representative of Rails in the daily business operations of the store and support all store initiatives set out by management including superior client engagement, store upkeep, operational support, ensuring visual standards while driving for sales results and KPI goals.

The Keyholder reports to the Store Manager.

Responsibilities:

Performance:

• Support floor coverage, financial targets, visual merchandising standards, client service, and operational functions within the store both front of house and back of house are achieved
• Be a support to execute business plans to accelerate the business forward and remedy opportunities
• Culture: Be an ambassador to the brand and promote the culture of Rails internally and externally
• Ensure store atmosphere upholds the image of the brand

Client Centric:

• Support the acquisition and retention of clients are key focuses and as such create and cultivate client relationships for the store and brand overall
• Be sure that you and your teams deliver the best possible client experience with every type of engagement (in store, virtual, alternate mediums)
• Follow through on customer journey as required to ensure a content client
• Support the needs of the client through styling advice and suggestion with every engagement
• Solution oriented approach to finding resolutions to customer service issues

Marketing & Community:

• In partnership with Store Management Team, bring to life activations/ events in the store that seek client acquisition and focus on client retention/ development

Team Leadership:

• In alignment with Store Management continually coach, motivate, train and develop internal teams so they achieve performance goals and are set up for success with growth opportunities within the organization
• Support a positive work environment with teams and throughout store network including cross functional partners
• Support performance management initiatives with store teams
• Attend and participate at store meetings as required by the business
• Ability to manage and resolve conflict in the workplace

Visuals:

• Support the image of the store and ensure that is in line with corporate standards and store team is upholding these standards

Operations:

• Support inventory functions as set out by Store Management including receipts, reconciliations and transfers
• Protect all company assets including cash handling, inventory, expenses etc.
• Support Client Consignment business, ensuring a quick turnaround, strong take rate, and timely return of merchandise
• Support omnichannel functions, including Order-in-Store, Ship-from-Store, Pickup-in-Store, Reserve-in-Store, with a focus on achieving Omni-specific KPIs
• Provide support to ensure that all processes are compliant with legal, safety, and internal procedures
• Partner with cross functional partners including Stores within network, Operations, Visual Team, CRM, Retail Training, HR, Merchandise teams, Regional management as necessary
• Additional projects/ responsibilities may arise in accordance with the needs of the business

Requirements:

• At least 1+ years of experience in a keyholder position preferred
• Fashion enthusiasts and retail experience within women’s and men’s apparel preferred
• Ability to effectively create, manage and adhere to deadlines
• Familiar with key retail performance indicators
• Adaptable, a sense of openness, active listener, and compassionate
• Advanced organizational skills, writing and communication skills
• Expertise in Microsoft Office 365 Suite
• Comfortable and savvy with computer technology, including PC and iOS devices
• Travel approximately 10% of the time
• Ability to climb ladders
• Ability to lift 25+ lbs.

Rails is committed to providing equal employment opportunities and building a diverse workplace in all its forms and considers candidates without regard to race, color, religion, age, gender identity, sexual orientation, national origin, disability status, veteran status or any other characteristic protected by applicable laws. As an equal opportunity employer we welcome and consider all qualified applicants.

The Opportunity

A distinguished, multi-generational Northeast specialty apparel retailer is seeking a Chief Merchandising Officer to lead merchandising strategy and drive the next chapter of growth. This is an exceptional opportunity to join a company with over a century of heritage—one that has built its reputation on the belief that lasting relationships matter more than transactions.

This role offers the rare chance to shape the future of a beloved institution while honoring the traditions that have made it iconic. You will join a leadership team that values integrity, authenticity, and a genuine commitment to both customers and team members.

As CMO, you will have full strategic ownership of multi-store merchandising and a growing e-commerce platform. You'll curate an exceptional product assortment, build and nurture vendor partnerships, and ensure every customer touchpoint reflects the company's commitment to quality and service excellence.

This is a confidential search. Company details will be shared with qualified candidates who meet the basic criteria.

Why This Role Matters

This isn't just another CMO position. You'll be joining a company where relationships are the foundation of everything—relationships with customers who have shopped with us for generations, with vendor partners who share our commitment to quality, and with team members who take pride in delivering exceptional experiences.

The ideal candidate understands that luxury retail is about more than product—it's about creating moments, building trust, and earning loyalty through consistent excellence. You appreciate the nuances of high-end customer service and recognize that every interaction is an opportunity to strengthen a relationship.

What You'll Do

Strategic Leadership

• Develop and execute a comprehensive merchandising strategy that balances heritage with innovation
• Own responsibility for merchandising operations across all channels
• Partner with ownership and senior leadership to shape company vision and long-term growth plans
• Identify market opportunities and emerging trends while staying true to brand identity

Product & Vendor Management

• Curate an exceptional assortment of premium brands that resonates with discerning customers
• Build and maintain strategic vendor partnerships, negotiating favorable terms while preserving relationships
• Optimize pricing strategies to maximize profitability while maintaining value perception
• Oversee inventory management with a focus on sales, turnover, GMROI, and sell-through optimization

Omnichannel Excellence

• Ensure seamless integration between physical stores and e-commerce platform
• Drive digital growth while maintaining the personalized experience that defines the brand
• Create compelling visual merchandising and presentation standards across all channels

Team Development

• Lead, mentor, and develop high-performing merchandising and buying teams
• Champion a culture of customer obsession and service excellence throughout the organization
• Establish training programs that reinforce premium service standards

What You'll Bring

Required Experience

• 10+ years of progressive retail experience with demonstrated success in buying, merchandising leadership, preferably in high-end or luxury markets
• Proven track record of driving profitable growth
• Assortment planning expertise with the ability to develop strategies that balance brand integrity with commercial success
• Vendor relationship management experience, building and maintaining strategic partnerships with premium brands
• Inventory management mastery, including turnover optimization, GMROI analysis, and comparable store sales growth
• Omnichannel experience successfully integrating brick-and-mortar and e-commerce strategies
• Bachelor's degree or equivalent experience
• Outstanding aesthetic sensibility and understanding of luxury market positioning

Preferred Qualifications

• High-end specialty retail or luxury brand experience with similar customer demographics
• Experience with family-owned or founder-led organizations
• Change leadership skills with proven ability to inspire followership and drive transformation
• Innovation mindset with experience implementing retail technologies and digital initiatives

Leadership Competencies

The ideal candidate will demonstrate:

• Strategic Intelligence: Combines analytical rigor with an intuitive understanding of customer needs and market dynamics
• Integrity & Values: Leads with authenticity and builds trust through consistent actions and transparent communication
• Customer Obsession: Deep understanding of luxury service standards and genuine passion for exceeding expectations
• Visionary Thinking: Sees possibilities others miss while maintaining practical focus on execution and results
• Communication Mastery: Articulates vision with clarity and conviction; listens actively and builds consensus
• Entrepreneurial Mindset: Hands-on leader who thrives in dynamic environments and embraces an ownership mentality
• Relationship Builder: Values long-term partnerships over short-term gains; earns trust through consistent follow-through

What We Offer

• Competitive Executive Compensation: Salary commensurate with experience plus a comprehensive benefits package
• Equity Opportunity: Ownership stake for the right individual who shares our vision for the future
• Legacy Leadership: The chance to shape the future of a beloved, iconic institution
• Values-Driven Culture: A collaborative, family-oriented environment where relationships and integrity matter
• Impact & Autonomy: Direct partnership with ownership and the opportunity to make meaningful strategic decisions

Ready to Join Our Legacy?

If you're a passionate retail leader who believes that exceptional service creates lasting relationships, and you want to help write the next chapter for a storied institution, we'd love to hear from you.

This role is ideal for someone who appreciates the value of heritage, understands the nuances of luxury retail, and possesses the vision and drive to lead a beloved brand into its next era of growth.

Apply now by submitting your resume as a Word or PDF file.

#RetailJobs #CMO #ChiefMerchandisingOfficer #LuxuryRetail #RetailLeadership #ExecutiveJobs #Merchandising #FashionRetail

ABOUT ISALIS

Isalis is a multi-brand, trend-driven clothing boutique with locations in San Francisco, New York City, and soon to be, Boston! We curate the best, sought-after brands — including Bec + Bridge, Simon Miller, Sandy Liang, Tyler McGillivary, and Danielle Guizio — to style alongside our own private label. Our stores should feel like you’re stepping into your dream closet and our goal is for our staff to make you feel like you’re shopping with a best friend. Founded in 2017, Isalis brings back the joy of boutique shopping, where style feels personal, and every piece tells a story.

We’re looking for a highly motivated Store Manager to run operations + lead the opening of this new location. This role blends leadership, customer engagement, team development, visual merchandising, and sales strategy. The Store Manager leads by example, models operational excellence, and helps cultivate a warm, customer-first culture.

**The expected start date for this role is March/April 2026**

THE QUALIFICATIONS

• 4+ years in retail management or team leadership
• A strong individual sense of style and love of fashion
• A client-centric approach to styling and relationship building
• A competitive yet collaborative mindset — you’re energized by goals
• Confidence in coaching others and leading daily floor direction
• Strong sales intuition — you know how to elevate transactions and motivate a team
• Experience with retail operations, POS systems, and visual merchandising
• Exceptional multitasking skills — able to balance customer needs, team direction, and operational priorities with ease
• High personal accountability and ability to self-manage

THE ROLE

Team Leadership & Development

• Responsible for hiring, onboarding, training, and scheduling
• Lead daily floor coverage and team communication
• Give real-time coaching and performance feedback
• Support staff development conversations and corrective action when needed

Customer Experience

• Model a warm, thoughtful, and elevated styling experience
• Support ongoing client outreach and nurture VIP customer relationships
• Handle customer concerns with grace and solution-oriented communication

Sales & Performance

• Help meet, exceed and communicate daily/weekly sales goals
• Coach the team on selling behaviors and maximizing basket size
• Review sales data and share insights with leadership

Visual Merchandising & Presentation

• Maintain floor moves, weekly merchandising updates, and new product launches
• Ensure the store feels fresh, inspiring, and aligned with brand standards

Operations & Inventory

• Oversee opening/closing procedures and general store upkeep
• Maintain inventory accuracy and shrink reduction practices
• Partner with the Merchandising and Operations teams to ensure healthy inventory levels

THE PERKS

• Pay Rate: $26–$29/hr based on experience
• Path to Growth: Opportunities for advancement based on performance and leadership potential
• Product Discount: Employee discounts on Isalis merchandise
• Career Development: Opportunity to be a influential part of a new store/new market opening with hands-on leadership experience in a fast-growing retail brand
• Community: Work alongside and network with like-minded, fashion-forward individuals who share your passion for style and boutique culture

AVAILABILITY AND COMMS

We’re seeking candidates available to work full time/40 hours per week, including weekend availability. Parking for a smaller vehicle is available on site.

When not on-site, you’re expected to stay up-to-date with company communications via email, text, and Slack.

TO APPLY

(If you're applying via LinkedIn, please also follow the steps below.)

Please email your resume and a cover letter to

In your cover letter, please include:

• Why you believe you’re a great fit for this role, including any relevant experience
• Any pre-scheduled time off in the next 3–6 months
• Your general weekly availability (days/times you’re unavailable)
• Your desired weekly hours

If you’re excited to lead with style, curiosity, and heart — and make an impact on a brand new store with Isalis Boston — we’d love to meet you!

ABOUT ISALIS

Isalis is a multi-brand, trend-driven clothing boutique with locations in San Francisco and New York City. We curate the best, sought-after brands — including Bec + Bridge, Simon Miller, Sandy Liang, Tyler McGillivary, and Danielle Guizio — to style alongside our own private label. Our stores should feel like you’re stepping into your dream closet — and our goal is for our staff to make you feel like you’re shopping with a best friend.

Founded in 2017, Isalis brings back the joy of boutique shopping — where style feels personal, and every piece tells a story.

We’re looking for a highly motivated Sales Associate to support daily operations at our New Boston location. This role focuses on customer engagement, styling, sales performance, and maintaining strong visual and operational standards on the floor. The Sales Associate leads with a client-first mindset, contributes to a positive team environment, and helps create a warm, elevated shopping experience for every customer.

THE QUALIFICATIONS

• A strong sense of individual style
• An client-centric approach to styling a unique range of clientele
• A passion for authentic connections and relationship building
• A desire to thrive in a high performance sales environment
• A strong sales intuition - you know when to push and upsell
• Worked in retail or service related industries
• A strong work ethic and the ability to autonomously manage responsibilities and workflow
• A relentless ability to close larger sales

THE ROLE

• Sell clothes and gain client confidence and loyalty through renowned styling expertise and authentic engagement with clients
• Be an expert on product and brand knowledge; keeping up on new arrivals, new brands and latest market trends
• Exceed sales goals daily, monthly, annually by helping clients find what they love through suggestive selling and building outfits that clients can’t live without
• Create the store energy, setting the tone for the customer experience from entrance to departure
• Maintain and exceed in-store presentation standards of merchandise and cleanliness, ensuring the right product is in the right place in the right quantities
• Accurately and efficiently process transactions while treating product with care and delivering a world-class client experience
• Use the register as a moment to further connect and identify upselling opportunities
• Mitigate theft opportunities through hands-on customer service involvement

THE PERKS

• Experience-based pay and performance based pay increases.
• Product Discount - Discounts on Isalis products
• Set Your Schedule - We will partner with you to align to your availability and preferred working hours (some limitations will apply)
• Career Progression - Our boutiques are a great place to kick start your retail career. Our leadership team is committed to your career growth and ambitions. We are prioritizing candidates who want to grow into Management quickly!

AVAILABILITY AND COMMS

• Seeking candidates looking to commit at least 15-25 hours weekly, with some regular weekend availability. Open and flexible to discussing availability for the individual.
• When not on site, we expect you to stay up-to-date with company communications and respond timely via email, text and Slack.

TO APPLY:

(after applying via LinkedIn, please also follow these steps below.)

Please email your resume and a cover letter to In your cover letter, please include:

• Why you believe you’re a great fit for this role, including any relevant experience
• Any pre-scheduled time off in the next 3-6 months
• Your general weekly availability (days/times you’re unavailable)
• The number of hours per week you're hoping to work

Additional Info:

• Pay rate will be based on experience
• Weekend availability is required
• Experience in retail apparel sales is preferred

About Topdrawer

Topdrawer designs tools for the impossibly creative.

Topdrawer was born in Tokyo and now operates 16 stunning stores across five major U.S. cities, with a growing direct-to-consumer luxury brand online. We serve a community of impossibly creative people with beautifully designed tools for living, traveling, and creating—fountain pens, notebooks, house shoes, small leather goods, sunglasses, bags, and ritual objects.

Our brand combines elevated Japanese design sensibility, European craft influences, and a uniquely personal retail experience that encourages presence, slowness, and intention. With strong in-store storytelling and an expanding digital presence, Topdrawer is evolving into a quiet powerhouse in modern luxury retail.

As Finance Manager, you will be a key member of Topdrawer’s home office leadership team, overseeing financial operations and supporting strategic growth across retail and e-commerce channels. Based in our Boston headquarters, you will manage day-to-day accounting and financial processes while partnering with leadership to provide insights, reporting, and forecasting that drive business decisions.

You are a detail-oriented financial professional with strong analytical skills, a hands-on approach, and a deep understanding of retail financial operations. You will ensure compliance, accuracy, and efficiency in all financial processes while also contributing to long-term planning, budgeting, and performance optimization.

Financial Management & Reporting

• Oversee all daily financial operations, including general ledger, accounts payable, accounts receivable, and payroll
• Prepare, analyze, and present monthly, quarterly, and annual financial reports for leadership and ownership
• Maintain accuracy and compliance in all financial records, adhering to GAAP and company standards
• Develop and monitor financial KPIs to track business performance

Budgeting & Forecasting

• Lead the annual budget process in collaboration with leadership
• Manage rolling forecasts, cash flow analysis, and variance reporting
• Provide financial modeling and scenario planning to support strategic initiatives

Business Partnership & Strategy

• Partner with Store Operations, E-commerce, HR, and Supply Chain to align financial processes with business goals
• Support decision-making with data-driven insights on sales, margin, and expense trends
• Identify opportunities for cost savings and operational efficiency across the business

Compliance & Controls

• Ensure compliance with federal, state, and local tax regulations
• Maintain internal controls and safeguard company assets
• Partner with external auditors and tax advisors to support filings and audits

• A financial professional with 5–7 years of accounting and finance experience (retail or consumer goods preferred)
• Experienced in budgeting, forecasting, and financial reporting, with strong knowledge of GAAP
• Proficient with accounting systems (NetSuite, QuickBooks, or similar) and Excel/Google Sheets at an advanced level
• Analytical, detail-oriented, and highly organized with excellent communication skills
• Comfortable working independently in a fast-paced, entrepreneurial environment while also collaborating cross-functionally
• Excited about design, sustainability, and supporting the growth of a creative, mission-driven brand

Be part of a global creative community rooted in timeless, functional design. Work for a mission-driven company that values originality, sustainability, and meaningful connections. Grow with a brand where your creativity, curiosity, and contributions truly matter.

• Salary Range: $90,000–$110,000 base depending on experience
• Bonus potential tied to company and individual performance
• Generous Employee Discount
• Vacation and Sick Leave
• Paid Holidays
• Medical, Dental, and Vision Insurance
• Flexible Spending Accounts (FSA) for Health and Dependent Care
• Company-Paid Short-Term Disability (STD), Long-Term Disability (LTD), and Life Insurance
• 401(k) Retirement Plan (IRA) with Company Matching
• Commuter Benefits

Topdrawer is an Equal Opportunity Employer and is proud to promote equal opportunity for all applicants without regard to race, color, religion, sex, sexual orientation, national origin, age, disability, military status, or any other applicable legally protected characteristic.

Physical Requirements: This role may require standing for extended periods and regularly lifting or moving items up to 50 lbs. Reasonable accommodations will be made to enable individuals with disabilities to perform essential job functions. If you need a reasonable accommodation during the application or hiring process, please contact

Applicants must be legally authorized to work in the United States. Topdrawer does not provide visa sponsorship for this position

We are seeking a motivated, high-energy Enterprise Software Sales Executive. This role focuses on acquiring new business within assigned accounts and vertical segments while managing the full sales cycle.

What You’ll Do

• Own and exceed quarterly revenue targets through new customer acquisition.
• Manage the full end-to-end sales cycle: prospecting → demos → contracting → close.
• Build trusted advisor relationships with prospects, clients, and partners.
• Create and execute strategic account plans with clear partner/alliance strategies.
• Collaborate with internal teams on billing, contracting, and payment collections.
• Leverage our global network of system integrators (GSIs) to drive sales campaigns.
• Deeply understand client processes to present compelling product solutions.
• Navigate complex, multi-stakeholder enterprise sales cycles.

What We’re Looking For

• 2–5 years of enterprise software sales experience (required).
• Background selling BPM, ECM, Case Management, low-code, automation, or SaaS solutions is a strong plus.
• Proven track record of meeting or exceeding quotas.
• Strong consultative selling ability with senior decision-makers.
• Self-starter with experience generating leads and building pipeline from scratch.
• Ability to work cross-functionally across geographically distributed teams.
• Bachelor’s degree required.
• Willingness to travel regionally (up to 70%).

• Competitive base salary of $100,000
• Uncapped commission averaging $75,000 annually (range $65,000–$85,000), paid weekly
• $7,800 annual car allowance to support daily travel
• Exclusive, high-value territory with long-standing customers
• High visibility role with direct impact on regional growth and product strategy
  
  

• Manage and grow all accounts within the assigned territory
• Develop new business while expanding existing customer relationships
• Conduct product demonstrations and support new lab startups
• Travel daily to customer sites and industry events
• Collaborate with internal teams and external partners to close opportunities
• Track quotes, report activity weekly, and exceed annual sales targets
  
  

• Bachelor’s degree required
• Proven success in outside sales and territory growth
• Comfortable managing complex, high-level customer relationships
• Strong technical aptitude and ability to learn a broad product portfolio
• Highly organized, self-directed, and travel-ready