Director, Sales

| Boston, MA, USA | Hybrid
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Job Description:
Role Summary
The Enterprise Sales Director is an influential sales leader overseeing a team of Enterprise focused sales representatives and is responsible for identifying, securing, servicing and strategizing key Enterprise business partnerships in the assigned region. This is an essential role in building, professionally developing, inspiring, and coaching the team; ensuring they reach their full selling potential, while expediting the expansion of the sales territories and Enterprise deal pipeline. This is an excellent opportunity to sell into the Human Resources industry and influence workplace cultures around the world; based on employee appreciation, connectedness, and gratitude.
Key Responsibilities

  • Leads all sales efforts in assigned East U.S. territories by forging relationships with key decision makers and assisting the team in creating long lasting partnerships in existing and new areas of business
  • Lead Enterprise sales team management and fulfilling all reporting requirements
  • Develop strategic and tactical plans delivered through a world class sales organization that continues to drive higher revenue, productivity and margin performance in line with Enterprise objectives
  • Hire, manage, and continuously professionally develop a world-class Enterprise East sales team to achieve success and meet overall goals
  • Effectively collaborate with cross-functional internal teams to drive sales success, strong communication, and true partnerships
  • Establish and track progress against agreed upon targets/KPIs, continuously reporting out on opportunities, trends, and planning ahead
  • Leverages the Challenger Sales Methodology to drive sales execution and deal progression
  • Deliver results and forecasts against targets
  • Acquires, retains, motivates and rewards an exceptional sales team to exceed business goals
  • As a key member of Workhuman's sales leadership team, work closely with sales leaders in defining the business strategic direction and planning activities
  • Help maintain and enhance a sales culture of innovation, determination, imagination and respect by driving affiliated behaviors in every interaction with the East sales team
  • Maintain a thorough understanding of the HR industry trends, technology, competitive landscape, and various HR personas related to CHRO's/VP's, Total Rewards and Talent.

Role Requirements

  • A proven leader in the HR industry space with the capability to instil excellence at all levels
  • Entrepreneurial, consultative, progressive thinker
  • Positive attitude with passion for helping others and driving accountability
  • 3+ years of having led outside field sales teams
  • Ability to recruit, lead, motivate, engage, and continuously assess high performance sales teams
  • 10+ years of experience in enterprise software SaaS sales
  • Passion for coaching, building, inspiring, and effectively managing sales teams
  • Ability to drive consistent growth within a set region and territory year over year
  • Proven sales expertise and solid, high level relationships at key accounts
  • Proven executive-level leadership skills in complex deal strategy, development, financial structuring, contract negotiations and closing with new clients
  • Demonstrated interpersonal skills, oral and written communication skills; ability to earn the right to be the room
  • Ability to travel to on-site prospect meetings and team offsites when needed within the East U.S. territories
  • Bachelor's degree preferred

Knowledge/Experience (Technical or professional information needed to perform role)

  • 3+ years of having led outside field sales teams
  • Ability to recruit, lead, motivate, engage, and continuously assess high performance sales teams
  • 10+ years of experience in enterprise software SaaS sales


  • Key competencies to consider (aligned with evaluation matrices) may be: Problem solving capability needed; Relationship building, judgement, strategic thinking.
  • Experience with various sales methodologies / Challenger preferred
  • Problem solving skills
  • Professional presentation skills
  • Excellent Relationship building skills with multiple levels inside an organization
  • Strategic thinking
  • Excellent listening skills
  • Excellent communication skills - verbal and written
  • Contract negotiation experience
  • Familiar with CRM systems, preferably SFDC


  • 3+ years of having led outside field sales teams
  • Ability to recruit, lead, motivate, engage, and continuously assess high performance sales teams
  • 10+ years of experience in enterprise software SaaS sales
  • Proven sales expertise and solid, high level relationships at key accounts
  • Proven executive-level leadership skills in complex deal strategy, development, financial structuring, contract negotiations and closing with new clients

The Company:
At Workhuman® our mission is to bring more humanity to the workplace. We recognise and embrace individuals' differences and believe that workforce diversity and inclusion are essential to our long-term growth and success. Even if you don't think you "check every single box" above, please still consider applying. We're looking for a human who is collaborative, and innovative with a growth mindset. We love what we do because we're shaping the future of work through our people and our technology. Our human cloud-based applications are helping some of the world's leading global brands connect culture to shared purpose. The Workhuman Cloud empowers employees to thank, talk and celebrate each other, creating an environment that sparks gratitude and human connection while increasing employee engagement and productivity.
Did you know we have an award-winning culture across EMEA and North America:

  • We were named as #5 Best Workplace in the Great Place to Work Awards in Ireland in 2022 in the large sized workplace category. We were also recognised as a Best Workplace for Women and a Best Workplace in Technology in 2020, 2021 and 2022.
  • In 2021 we were named as #2 Best Workplace in Europe in the medium sized workplace category.
  • We were also recognised as #2 Best Large Places to Work in Boston by Built In for 2023 as well as a Best Place to Work in Boston, U.S. Best Large Places to Work and U.S. Best Places to Work.
  • There are currently over 7.5 million users on the Workhuman® cloud across 180 countries.
  • Our core values are Respect, Determination, Innovation and Imagination.

Workhuman is an Equal Opportunity Employer and is committed to the principle of equal employment opportunity for all employees. We proudly provide a work environment free of discrimination and harassment. Employment decisions at Workhuman are based on solely on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social, or ethnic origin, sex (including pregnancy), age, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, or any other status protected by the laws or regulations in the locations where we operate. Workhuman believes that diversity and inclusion among our teammates is critical to our success as a global company, and we seek to recruit, develop and retain the most talented people from a diverse candidate pool.

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Technology we use

  • Product
  • Sales & Marketing
  • People Operations
    • CanvaDesign
    • IllustratorDesign
    • MiroDesign
    • ConfluenceManagement
    • HootsuiteCMS
    • WordpressCMS
    • Chorus.AICRM
    • DocuSignCRM
    • LinkedIn SalesNavigatorCRM
    • OutreachCRM
    • SalesforceCRM
    • MarketoLead Gen
    • ZoomInfoLead Gen
    • Microsoft TeamsCollaboration
    • SlackCollaboration
    • ZoomCollaboration
    • TrelloProject Management


We're located on Crossing Boulevard, right off of Rt. 9 in Framingham. Our office is easily accessible from Rt. 9, Rt. 495, and Rt. 90.

An Insider's view of Workhuman

What's something quirky about your company?

I think there are numerous things that are quirky about our company, all of them great! This company stands out in having created a culture that values the human connection. We’ve created an atmosphere of promoting each other, of being each other’s biggest champions, and making sure we all thrive and develop into the best versions of ourselves.


Director, Workplace Experience

How do you collaborate with other teams in the company?

Collaboration is a core part of our team’s daily life; we work closely with everyone from Product Management and Engineering to Customer Success and Sales. With the teams split between Framingham and Dublin, we’re regularly using new tools with different teams to improve our ability to brainstorm and communicate user flows.


Director, Product Strategy

How has your career grown since starting at the company?

I started my business development role here with just 6 months of software sales experience. My manager knew my aspirations of becoming a Sales Exec. and helped me achieve this goal in less than 2 years. At Workhuman, not only are you given the technology to be successful, but you have amazing resources around you to grow professionally.


Corporate Sales Executive

What unique initiatives do you have that encourage innovation?

These days, we are dealing with a variety of stresses and change is constant. One of the most powerful ways to align teams and help people reach their full potential is so simple and can be easily missed- recognize an employee for their contributions! That positive connection carries far beyond the moment it occurs.


SVP, Global Sales

What's the biggest problem your team is solving?

Workhuman is not only in the business of changing the future of work for other companies, we are already thriving in that state ourselves. It’s so exciting to join a group of brilliantly passionate employees who are genuine, kind, and grateful to each other and working together on our mission to bring others into this human movement.


People Analytics Consultant

What are Workhuman Perks + Benefits

Workhuman Benefits Overview

There are a lot of benefits to working human, but let’s start with the most meaningful. We value the whole human – not just what you bring to the office every day, but everything about you and who you are. Here, people are empowered to be themselves and do the best work of their lives.

Volunteer in local community
Employees are encouraged to plan and participate in philanthropic activities through the Workhuman Gives program. 8 hours of paid volunteer tour
Partners with nonprofits
Previous partnerships have included Catie's Closet, Girls Inc., Tech Gives Back, and the Department of Child and Family Services.
Open door policy
OKR operational model
Team based strategic planning
Open office floor plan
Employee resource groups
Hybrid work model
President's club
Employee awards
Flexible work schedule
Workhuman encourages employees to find the work-life blend that meets their needs.
Remote work program
Documented equal pay policy
Dedicated diversity and inclusion staff
Mandated unconscious bias training
Mean gender pay gap below 10%
Diversity employee resource groups
Our ERGs are something we are very proud of! We have 5 ERGs running including: Parents at Workhuman, The Women's Network, SPARKLE (LGBTQIA+), Sustainability, and Diversity, Equity & Inclusion.
Hiring practices that promote diversity
Health Insurance + Wellness
Flexible Spending Account (FSA)
Disability insurance
Short term and long term disability benefits are available
Dental insurance
Vision insurance
Health insurance
Health insurance is provided by Blue Cross Blue Shield of MA and includes prescription drug coverage. Workhuman also provides deductible reimbursements via our health reimbursement arrangement.
Life insurance
Pet insurance
Wellness programs
Team workouts
Mental health benefits
Financial & Retirement
401(K) matching
Eligibility rules apply.
Company equity
RSU grant
Performance bonus
Child Care & Parental Leave
Childcare benefits
Dependant Day Care FSA Available
Generous parental leave
We provide up to 12 weeks of parental leave for the primary caretaker. Workhuman also provides 4 weeks of leave for the secondary caretaker, or for adoption/foster.
Family medical leave
Adoption Assistance
Company sponsored family events
Workhuman hosts seasonal events where employees can invite their family members and children to attend.
Vacation + Time Off
Generous PTO
Paid volunteer time
Paid holidays
Paid sick days
Office Perks
Company-sponsored outings
Free daily meals
Free snacks and drinks
Some meals provided
Onsite office parking
Recreational clubs
Fitness stipend
Home-office stipend for remote employees
Onsite gym
Professional Development
Job training & conferences
Tuition reimbursement
Lunch and learns
Promote from within
Continuing education stipend
Continuing education available during work hours
Online course subscriptions available
Customized development tracks
Paid industry certifications

Additional Perks + Benefits

In addition to our compensation and benefit offerings, employees are able to fully immerse themselves into our product.

As superusers of our own social recognition platform, our employees are constantly being recognized for their efforts at work by their managers and company leaders, as well as their colleagues and peers. We celebrate success in the office and outside of the office with our Life Events tool, and our Conversations tool gives employees the ability to navigate their priorities and goals, give and receive feedback, and manage check team check ins.

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