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Sr. Account Executive

Actionstep

Chicago, Illinois, United States Remote permanent

Posted: June 6, 2025

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Quick Summary

We are seeking a highly motivated and results-driven Sr. Account Executive to join our dynamic team in Chicago, IL. The ideal candidate should have excellent communication skills, a proven track record of building strong customer relationships and a deep understanding of the Legal Practice Management software. Key skills required include excellent communication skills, sales acumen, and the ability to work in a fast-paced environment.

Job Description

Actionstep is a pioneer in the development and sale of software-as-a-service (SaaS) products, specializing in the delivery of Legal Practice Management software. We are a fast growing, dynamic business with a global customer base of more the 30,000 and a team of over 180 in the USA, Australia, UK, Canada and New Zealand.   

The Sales Team is essential for building strong customer and partner relationships that enable the achievement of business targets. To project a positive first impression of Actionstep that accurately represents the Actionstep product and value proposition. To clearly articulate how at a strategic level Actionstep can enable our customers the opportunity to be successful, through giving them the time and freedom to focus on what they do best; ‘be lawyers’. To continuously improve and develop relevant and fit for purpose sales methodology and capability across the entire sales function. 

The Account Executive serves as a key driver of revenue growth and client success in Actionstep’s Sales Team, playing a vital role in acquiring, retaining, and expanding the customer base.

The Account Executive will grow the Actionstep customer base and meet revenue and login targets through successful sales delivery of the Actionstep value proposition. To collaborate effectively with Marketing and other Customer Growth team members to effectively promote and market Actionstep as a competitive solution within the legal industry. 

Success of the Account Executive will be measured primarily by revenue generation following customer acquisition and login growth. Secondary measures of success will include, qualified lead generation and delivery of outbound sales activity.  

In this role, you will be accountable for…

Customer Growth:

• Meeting and exceeding individual monthly and annual targets with the view to build the Actionstep customer login numbers, generate revenue and contribute to total business KPI’s. 

• Prospecting and developing relationships in key customer groups and regions, to generate sales opportunities and grow the customer base.  

• Reviewing and qualifying all inbound leads in line with Actionstep qualification criteria and across a variety of channels.  

• Effectively nurture and leverage business from new and established customer relationships, associations, and network groups 

• Effectively manage customers through the Actionstep sales process ensuring adoption as required. 

• Leading effective Actionstep demonstrations ensuring clear and concise communication. 

• Actively leverage Actionstep sales tools, systems and process (ie hubspot, LinkedIN Navigator) to identify, record/track, connect and qualify potential customers. 

• Proactively research and perform outbound based activities for key customer group with the goal of generating new customer leads. 

General Sales & Marketing:

• Working collaboratively with Marketing, Product and in-region Customer Growth team members to bring market insights and marketing ideas to assist in the execution of a sales strategy.  

• Proactively seeking out networking opportunities, participation in industry events, webinars, and user groups to develop personal and Actionstep profile and interest in the market. 

• Championing and advocating the Actionstep legal practice management platform and value proposition within region. 

• Activity contributing to the effective delivery of Marketing campaigns and activities (i.e events/webinars etc..). 

• Actively contributing to continuous improvement activities that enhance and support the effective evolution of the Actionstep sales process and methodology.  

Reporting & Administration:

• Recording and maintaining a regular and accurate sales pipeline through tracking relevant metrics and notes within Actionstep’s CRM (Hubspot). 

• Complying with all monthly, quarterly, and ad-hoc reporting requests, as and when requested. 

• Escalating all financial discrepancies, risks, and customer challenges (i.e. potential credits) to Regional Vice President.  

Relationship Management:

• Building and maintaining strong working relationships with all internal and external parties ensuring transparent, proactive and effective communication always.

• Attending and proactively contributing to customer, partner and internal meetings with the view to add value in a constructive manner.

Professional Development:

• Actively looking to build own career through delivery of self and assisted professional development initiatives.

• Being a thought leader both within Actionstep but also in the wider industry.

• Staying abreast of industry best practice patterns, products and technologies and assisting in process improvement activities as required.

Continuous Improvement:

• Proactively in identifying and participating in the continuous improvement of processes and procedures within the ​Relevant Team​ department.

• Actively contribute to the development and maintenance of a strong department culture ensuring knowledge and experience is shared.


Requirements:
WHO ARE YOU

Excellent Communicator: You are comfortable communicating with customers and internal teams and saying no when you need to.  

Relationship Builder: You have strong skills in cultivating and maintaining relationships with clients is crucial for success by being personable, empathetic, and able to understand clients' needs.

Negotiator: You can negotiate terms, contracts, and pricing that strikes deals that benefit both the client and Actionstep.

Problem Solver: You are proactive and resourceful in resolving issues.

Strategic Thinker: You understand the broader business goals and aligning them with client objectives by analysing data, identifying opportunities, and devising plans for growth.

WHAT YOU NEED TO KNOW AND WHAT WILL HELP MAKE YOU SUCCESSFUL

Experience & Qualifications:

Essential:

• 5+ years of relevant sales experience. 

• Exposure and knowledge of the legal industry. 

• Experience presenting and leading product demonstrations. 

• Experience working in a SaaS technology environment. 

• Achievement of or working towards a relevant sales methodology certification. 

Desirable:

• Experience coaching and mentoring others on all things sales.

Personal Skills, Attributes & Behavioural Competencies:

• Highly self-motivated and driven by achieving results and hitting targets. 

• Ability to work in a fast-paced environment with minimal supervision. 

• Has the ability to qualify, drive and close opportunities. 

• Ability to build and maintain strong working relationships.

• Maintains clear and concise written and verbal communication, builds rapport, listens well, asks questions to clarify customer needs and adapts style and approach to suit. 

• Highly organised with an ability to manage multiple priorities in an efficient manner. 

• Able to lead demonstrations and deliver effective presentations. 

• Able to work autonomously yet contribute effectively as a team player. 

Other:

• Suitable Criminal Record Check.


Benefits:
We have a fantastic and inspirational working environment!

• Robust medical, dental, vision offerings
• 401K with company match
• Flexible working and PTO
• Take your birthday off
• Frequent team building events
• Fantastic training and development opportunities

• 130k Base + Competitive variable

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