About this role.
This Enterprise Sales Executive role at QuinStreet focuses on driving high-value, complex sales cycles with enterprise-level contractors and remodeling organizations. The position requires strategic advisory skills to help C-suite executives scale their businesses through tailored digital marketing solutions. Responsibilities include owning the full sales process from prospecting to closing six and seven-figure contracts, using methodologies like MEDDIC, and collaborating with internal teams. The ideal candidate has over 7 years of top-performing inside sales experience and a proven track record of exceeding quotas. This is a high-impact, fast-paced role with significant earning potential and visibility across leadership.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Manager,
I am excited to apply for the Enterprise Sales Executive position at QuinStreet. With over 7 years of top-performing inside sales experience and a consistent record of closing six and seven-figure contracts, I have developed the strategic and consultative skills needed to drive success in complex enterprise sales cycles. My expertise in MEDDIC and outbound prospecting has enabled me to build robust pipelines and engage C-suite executives effectively. I am particularly drawn to QuinStreet's innovative performance marketing platform and am eager to leverage my skills to help clients scale their businesses. Thank you for considering my application; I look forward to contributing to your team's success.
Sample interview questions
I start by thoroughly researching the prospect's business, identifying key stakeholders and their priorities. I use MEDDIC to qualify and align with the customer's objectives, then build a multi-threaded relationship across the organization. Throughout the cycle, I provide value through insights and tailored solutions, while consistently driving momentum and managing expectations to close within the timeline.
In a previous role, I was negotiating a $1.5M annual contract with a national home services company. My strategy was to understand their financial drivers and ROI expectations, then build a compelling business case using pro-formas. I focused on win-win outcomes by structuring the deal with flexible terms and performance-based pricing, which ultimately led to a signed agreement and a long-term partnership.
I view rejection as a learning opportunity and maintain a disciplined pipeline to ensure a steady flow of opportunities. I stay focused on the end goal and break the sales cycle into smaller milestones, celebrating each win. Additionally, I rely on my grit and persistence, knowing that enterprise deals often require multiple touchpoints and stakeholder buy-in.
I use a combination of personalized cold emails, targeted phone calls, and social selling on LinkedIn. My approach is to provide relevant insights and industry best practices that resonate with their business challenges. I also collaborate with marketing to run Account Based Marketing campaigns for key accounts, ensuring a coordinated and value-driven outreach.
I maintain strict pipeline hygiene in Salesforce, updating deal stages and next steps after every interaction. I review my pipeline weekly to identify risks and opportunities, using historical win rates and deal velocity to forecast accurately. By consistently qualifying deals against MEDDIC criteria, I ensure that my forecast reflects realistic revenue expectations.
Powering Performance Marketplaces in Digital Media
QuinStreet is a pioneer in powering decentralized online marketplaces that match searchers and “research and compare” consumers with brands. We run these virtual- and private-label marketplaces in one of the nation’s largest media networks.
Our industry leading segmentation and AI-driven matching technologies help consumers find better solutions and brands faster. They allow brands to target and reach in-market customer prospects with pinpoint segment-by-segment accuracy, and to pay only for performance results.
Our campaign-results-driven matching decision engines and optimization algorithms are built from over 20 years and billions of dollars of online media experience.
We believe in:
- The direct measurability of digital media.
- Performance marketing. (We pioneered it.)
- The advantages of technology.
We bring all this together to deliver truly great results for consumers and brands in the world’s biggest channel.
Job Summary
As an Enterprise Sales Executive, you will own and drive high-value, complex sales cycles with enterprise-level contractors and remodeling organizations. This role goes beyond transactional selling. You will act as a strategic advisor to executive stakeholders, helping them scale their businesses through tailored solutions.
You will lead 2–6-month sales cycles, navigate multi-threaded deals, and consistently close six and seven-figure contracts. Leveraging methodologies such as MEDDIC, you will align customer business objectives with Modernize solutions and partner cross-functionally to deliver long-term value.
This is a high-impact role with visibility across leadership, requiring a combination of strategic thinking, executive presence, and consistent quota overachievement.
Responsibilities
- Drive sales revenue through new client acquisition signing $2M+ in annual business
- Gain a deep understanding of our ICP (ideal customer profile) and target that market
- Outbound/cold emailing/calling key decision makers within target accounts to generate opportunities
- Preparing and managing a robust sales pipeline with a win rate of ~30% and closing within a 1–6-month sales cycle
- Prospect into the C-Suite at companies sized between $30M-$500M+, driving engagement, value, and new business
- Work with Demand Generation leadership to develop and drive Account Based Marketing strategies for biggest opportunities in your pipeline
- Partner with Account Management teams to hand off landed business for expansion
- Negotiating successfully with expert buyers to win meaningful contract value, with ideal customers
- Maintain pipeline hygiene in SFDC for weekly forecasting purposes
- Educate clients on industry best practices to use leads, as well as other digital marketing channels.
Experience
- 7+ years of experience as a top performer working in an inside/virtual sales environment
- 5+ years of experience closing six and seven figure business
- 5+ years of experience in contract/term negotiations driving win/win outcomes
- Expert in virtual sales technology and prospecting tools
- Proven success building engagement campaigns to drive awareness at the top of the funnel
- Expert at adding value to prospects from prospecting to close
- In Depth understand of pro-formas and ROI — financial knowledge is power
- Phenomenal expectation setting and rapport building
- Expert active listener, assertive, persistent, and persuasive – show us your grit!
- The will to win all the way attitude
- Collaborative, agile, competitive, and coachable
- An understanding of and experience in startup-level hard work
- Sales Rock Star with a proven history consistently blowing out sales quotas and objectives
- Self-driven, results-oriented optimist with a clear focus on quality and business performance – you do the right things the right way.
- Interpersonal communication guru – excellent written/verbal communication and customer relationship skills. Someone who knows how to have difficult conversations.
- Constantly improving your sales acumen
QuinStreet is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, national origin, pregnancy status, sex, age, marital status, disability, sexual orientation, gender identity or any other characteristics protected by law.
Please see QuinStreet’s Employee Privacy Notice here.
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