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VP of Inside Sales

Do you currently manage a top performing Inside Sales team at an enterprise software company -  but wish you could expand your skills across multiple companies, products and industries instead?


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VP of Inside Sales
$200,000 USD Per Year



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Are you relentless at productivity metrics for your Inside Sales teams to drive even more sales daily?  Do you wish you were working in a fast-growing private equity firm acquiring numerous enterprise software companies - then relying on you to make their renewals inside sales teams world-class?  If so - this role is for you. 

In our enterprise software space, customer success is the heart of the business - and annual renewals and Platinum support are how these customers show us how they really value our products.  Your job as the VP of Inside Sales will be to manage a team of Inside Sales Reps that will talk to our customers, get them excited about our vision and our products, understand their needs - then convince them to renew their enterprise software license and sell up to our Platinum support.  Your role will expand across the our family of companies and you will be expected to continuously drive increased productivity and effectiveness of your team.


To be effective in this role - you must wake-up everyday believing that the team can continue to get better through process improvements, content improvements, cross-training and topgrading.  You must be a hands-on coach to your team - and extremely metrics-oriented.  You will be asked to sell renewals and Platinum upsells across many of our companies - so you will also need to be able to learn each of these products in detail and help your team as they learn various product lines.  You must be an experienced Inside Sales manager to continually introduce innovative methods to make your reps world-class.  



Key Responsibilities

  • Drive a team of Inside Sales reps that will be responsible for closing customer enterprise software renewals across the our family of companies

  • Relentlessly pursue team productivity gains through better content, training, coaching and use of new technology tools

  • Innovate on process and tools to help your Inside Sales teams close renewals and upsells more effectively

  • Serve as the senior line of escalation to be able to explain to customers the benefits of Platinum support and the impact on customer success - then close Platinum upsells

  • For companies we acquire - sell the vision to customers on the benefits of that company becoming a part of our family of companies

  • Ramp your Inside Sales team to effectively learn and be able to sell renewals on new products as the company acquires additional companies

  • Build relationships with prospects and internal stakeholders to grow new business

  • Prospect, nurture and close new business at or above Quota

  • Build relationships with prospects and internal stakeholders to grow new business

  • Generate opportunities, manage pipeline and deliver accurate forecasts using SalesForce CRM

Candidate Requirements

  • 10+ years of enterprise software sales experience

  • 7+ years managing metrics-based Inside Sales teams

  • Demonstrated success exceeding new business quota

  • Experience with sales operations & contract negotiation

  • Strong organizational skills & highly coachable

  • A passion for the high-growth environment

Who Is Crossover?

Crossover connects the world's top talent with the world's best companies. We're re-inventing how people find long-term, challenging work, and how companies leverage the best talent in the world. We assemble teams of rockstars and provide playbooks and a platform, WorkSmart, to help teams and individuals continuously improve how they work.

We're creating a future where all high-skill jobs are in the cloud and big data helps people and teams be more productive. A future where brick and mortar offices are history. We believe the future of the workforce is global and will be built from teams collaborating from every corner of the world.

Crossover has more than 2,500 partners in 108 countries. Unlike freelancer or outsourced marketplaces, Crossover only offers long-term, multi-year projects or programs.

Hear more about our strategy and vision from our CEO, Andy Tryba: 


The Remote Life @ Crossover.

A key benefit of Crossover - and the cloud - is all our roles are location independent. Live and work anywhere: work from home, a coffee shop or at one of the many co-working spaces Crossover partners can access and collaborate.

 Work from a home office or co-work at the many co-working spaces available to partners around the world

Work from a home office or co-work at the many co-working spaces available to partners around the world

We believe in equipping people to work where they can be the most productive and happy, with a commitment of 40 hours a week.

Crossover offers:







Step 1: Online Application

Start your application by creating an account and profile with Crossover, then uploading your resume and confirming your email address. From there, the Crossover platform will guide you through the remaining steps.


Step 2: Take the English and Fundamentals Test

We have a series of multiple-choice tests to check for the knowledge and skills needed for the role and an English exam where we ask candidates to upload a 2-3 minute audio submission. After this stage, you will receive an email invitation to the next step in the application process.

Step 3: Free Response Questions and CCAT Testing

In this step, we will ask you a series of free response questions that will simulate scenarios you are likely to encounter in the role. We find both the willingness to invest this time – coupled with the insights we derive from the answers – help us find the truly capable and passionate candidates. You may also be asked to make a presentation of your answers to demonstrate your communication skills. The free response section is an opportunity to preview the type of work you would be doing in the role and demonstrate your technical skills and abilities to hiring managers. The last free response question will invite you to complete CCAT testing. The CCAT measures cognitive aptitude or general intelligence, and tests an ability to solve problems, digest and apply information, learn new skills, and think critically.

Step 4: Join the Interview

The final step of the evaluation process is the marketplace interview. One of our hiring manager evaluators will speak with you on a video call to understand if you're the best fit for the position. In addition to technical and business questions about your current and previous roles and achievements, you may be asked about the answers you gave in your free response questions.

Step 5: Meet the Customer and Get Hired

If you successfully pass all stages of the evaluation process, you will have the opportunity to talk with hiring managers about the positions that are currently available. This is intended to be a two-way discussion where you can ask questions about the team, product, metrics, roadmap, etc. You can interview with as many hiring managers as desired and make the decision on which company or team best fits your interests and career goals.