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Invoice Cloud, Inc.

Enterprise Sales Director - Financial Services

Braintree, MA

About InvoiceCloud

InvoiceCloud, an EngageSmart solution, is a leading provider of online bill payment services. Founded in 2009, the company has grown to be one of the leading disruptors in the cloud-based electronic bill presentment and payment (EBPP) space, helping institutions put customer experience first. By switching to InvoiceCloud, clients can improve customer engagement, loyalty, and efficiency while reducing churn and missed payments in the process. With over 50 million payments processed annually, InvoiceCloud is one of the most secure, innovative, and inclusive fintech solutions in the market. To learn more, visit

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The Enterprise Sales Director (ESD) is responsible as an individual contributor as well as specific target markets for the Financial Services Vertical (P&C Carriers + Consumer Finance Firms). The ESD is accountable for creating and making the monthly, quarterly and annual sales plan for that region and vertical market. Working closely with the Invoice Cloud Partner Manager, responsibilities also include the ongoing identification and development of new partnership opportunities in their region.

What You'll Do:

First 30 days – Assess the current situation and build a framework as follows:

  • Gain a strong understanding of the Invoice Cloud (IC) solution and our market approach
  • Undergo IC Sales Territory Training session
  • Develop a comprehensive understanding of the IC Value Proposition
  • Understand GAP Selling methodology
  • Gain an understanding of the current and future opportunities in their specific geographic region
  • Learn the details of the existing IC integrations and partners and their presence in the region
  • Become proficient in the IC Sales Tools including
  • Develop presentation and proposal materials based on IC Sales Library
  • Determine and document regional trade shows and conferences that will build a network of opportunities in your region
  • Travel with two existing sales reps to watch demo’s and in person meeting cadence
  • Take notes on meeting and provide constructive criticism on what went well and what could be done better
  • Document the IC End to End Sales Process from lead generation through installation and account management
  • Identify the top three key partners in your region and appropriate contacts

First 60 days – begin execution regional sales plan

  • Create a detailed territory plan for getting to “Goal”, including forming partnerships, building pipeline, monthly/annual goals, etc
  • Attend regional conferences and trade shows for networking opportunities
  • Begin working with existing partners in the region and developing relationships with existing IC clients in region
  • Begin to build a sustainable pipeline for reaching goal
  • Maintain key position of Invoice Cloud within the territory.  Attend key conferences and manage list of existing accounts (provided) and grow new account base.
  • Partners – Work with existing partners doing business in territory and cultivate new partnership relations. Meet with the three key partners identified previously.
  • Execute GAP Selling methodology

First 120 days – Mature in regional market

  • Begin regularly hitting required demo metrics on a monthly basis: 10 new prospect demos per month
  • Close business with existing partner clients
  • Establish top 20 prospects in region

First 180 days  Maturing pipeline

  • Develop a pipeline of at least 35 qualified opportunities

First 270 days – begin the smoothing out process

  • Begin to close business on a regular basis (min 1 deal or 15,000 bills per month)
  • Identify solid forecasting for rolling three-month period

What We Seek:

  • Min 4-5+ year of enterprise sales experience in software/technology that requires a consultative sales approach.
  • Experience as an autonomous contributor working from home
  • Ability to generate leads/opportunities through partnerships and otherwise
  • Ability to match client problems with Invoice Cloud product
  • Well organized with very strong time management skills
  • Strong work ethic
  • Strong planning and execution skills
  • Ability to Identify, target, present, demonstrate and close prospective billing organizations in the territory
  • Meet the assigned sales targets on a monthly, quarterly and annual basis
  • Actively show a commitment to professional selling, where personal respect, integrity and ethical business practices are first and foremost
  • Manage growth, sales pipeline and accurate forecasting
  • Identify and implement strategic partnerships and initiatives focused on increasing revenue and Invoice Cloud’s value
  • Effectively work in the Invoice Cloud team to bring prospect and customer service opportunities forward 

Base Compensation Range: $145,00 to $150,000 annually. Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission and equity. Some roles may also be eligible for overtime pay. The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we’ll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.


We offer a competitive benefits program including:

  • Medical, dental, vision, life & disability insurance
  • 401(k) plan with company match 
  • Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
  • Mental health resources
  • Paid parental leave & Backup Care
  • Tuition reimbursement
  • Employee Resource Groups (ERGs)

Invoice Cloud is an Equal Opportunity Employer. 

Invoice Cloud provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.  

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.  

If you have a disability under the Americans with Disabilities Act or similar law, or you require a religious accommodation, and you wish to discuss potential accommodations related to applying for employment at our company, please contact

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To all recruitment agencies: Invoice Cloud does not accept agency resumes. Please do not forward resumes to our job’s alias, employees, or any other organization location. Invoice Cloud is not responsible for any fees related to unsolicited resumes.  

Client-provided location(s): Braintree, MA, USA
Job ID: 5891714003
Employment Type: Other