Head of Sales

| Chicago

Sertifi is the leader in Frictionless Business, with innovative solutions for modernizing the last mile of the sales process. Sertifi offers the fastest and most secure way to close business, from eSignatures to online payment capture. Thousands of companies around the world trust Sertifi to close more deals faster, recognize revenue quickly, enhance security and compliance, and go completely paperless. 


Sertifi is looking for a driven, invested and experienced Head of Sales to join our growing team. You will be responsible for leading and scaling our sales organization and driving company growth. We have been growing at a rate of over 50% YOY, and we’re looking for someone to take us to the next level. 


As the Head of Sales, you will be in charge of managing a team of 10+ people, executing company revenue goals, facilitating our sales processes, and scaling the team. You will get to know our customers, work with our strategic partners, and manage key accounts. Our ideal candidate is an inspiring sales leader who is passionate and experienced in developing a high performing sales organization. We’re looking for a doer – someone who can get things done while moving the business forward. This position is located in our downtown Chicago office and reports directly to our Co-Founder. 


Challenges You’ll Tackle: 

  • Lead of a team of 10+ Account Executives and Business Development Reps to achieve aggressive revenue goals
  • Be a hands-on leader by assisting with introductions, advancing deals in the sales process, or closing the accounts
  • Build out the sales team: recruit, train and develop talent
  • Plan and execute high impact weekly sales meetings and 1:1s to measure performance
  • Responsible for our sales operations including pipeline management, forecasting, compensation plans, and sales playbook
  • Work with leadership to build a scalable and repeatable sales process
  • Learn the ins and outs of our product and target markets so you can provide expertise to our sales team and represent Sertifi at industry events
  • Maintain and foster amazing relationships with customers; gain a deep understanding of our customer’s organizational and business needs 
  • Build strong ties with internal teams like Marketing, Product, Customer Success and Finance to ensure alignment
  • Maintain a fun and high-performance team culture that celebrates success


What You’ll Need to Succeed: 

  • 7+ years of experience successfully managing and growing a sales team
  • B2B SaaS experience, preferably at a startup or growth phase company 
  • Proven track record of exceeding quotas, both personally and as a sales leader 
  • Hands-on involvement in growing a company 50-60% YOY 
  • Demonstrated ability in sales leadership: ability to develop and coach team members  
  • Excellent communicator; strong verbal and written communication and presentation skills; effective at delivering high-level demos and presentations  
  • High degree of emotional intelligence and ability to know the strengths of your team 
  • Proficiency with Salesforce.com including reporting and managing KPIs 
  • Bachelor’s degree required  
  • Ability to travel 10-12 times per year or as needed for sales meetings or trade shows 


Attributes We Value: 

  • Leadership – you have the ability to communicate our vision, reflect the values of Sertifi, demonstrate integrity, and set an example of positive leadership for the team 
  • Collaboration – you know how to work with different types of people and personalities and thrive on achieving goals as part of a team effort  
  • No task too small attitude – you’re not afraid to roll up your sleeves and “do what it takes” to get the job done 
  • Confidence – you have confidence in yourself and your team, but never an ego; you’re comfortable pushing boundaries to drive success 
  • Motivation – you are capable of motivating people at every level to hit their goals and perform at their best  
  • Resourceful – you have the ability to make things happen in creative ways despite a lack of resources 


What’s in it for you:  

You will work in a collaborative office environment that welcomes new ideas and allows you to make an immediate impact on the team. Additionally, we offer great benefits such as: competitive salary, health/dental/vision insurance, 401k with company match, paid parental leave, pre-tax Transit Benefit Program, casual work environment, weekly team lunches, company outings, and a convenient River North location close to public transit.  

Read Full Job Description

Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • .NETLanguages
    • C#Languages
    • SqlLanguages
    • AzureLanguages
    • ASP.NETFrameworks
    • ASP.NET CoreFrameworks
    • AngularFrameworks
    • Microsoft SQL ServerDatabases
    • Azure Cosmos DBDatabases
    • BalsamiqDesign
    • ConfluenceManagement
    • JIRAManagement
    • WordpressCMS
    • SalesforceCRM


350 North LaSalle, Chicago, IL 60654

An Insider's view of Sertifi

What does your typical day look like?

After getting some coffee and catching up on emails, I’ll typically have a few clients that need onboarding help! This consists of me discussing their workflows and what action is needed for them to be live using Sertifi. If we’re not discussing set up, I’m either training a team on how to use the system, or creating web portals for new clients!


Customer Success Manager

What are Sertifi Perks + Benefits

Health Insurance & Wellness Benefits
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Retirement & Stock Options Benefits
401(K) Matching
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Vacation & Time Off Benefits
Generous PTO
Paid Holidays
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Some Meals Provided
Happy Hours
Relocation Assistance
Professional Development Benefits
Job Training & Conferences
More Jobs at Sertifi9 open jobs
All Jobs
Design + UX
Dev + Engineer
Design + UX