Mid-Market Account Executive - Chicago

Legora

ABOUT US Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar. Our AI-native workspace lets legal professionals move faster, think more clearly, and operate with sharper precision. By analysing thousands of documents in minutes and powering end-to-end workflows, we cut through complexity, teams can focus on what matters: judgment, strategy, and outcomes. 1,000+ customers across 50+ countries trust us, including Cleary Gottlieb, Goodwin, Linklaters, White & Case, Dentons, and Barclays. We’ve scaled to $100M+ in ARR, with teams across Europe, North America and APAC, and continue to expand through acquisitions including Qura, Walter AI and Graceview. We partner with world-class performers: including Aaron Judge and the New York Yankees, Ludvig Åberg (and his caddie), and campaigns featuring Jude Law. Joining Legora means three things. * We lean in: ownership over titles, outcomes over intentions. * We fight for excellence: high standards, direct, ego-free feedback. * We grow together: as a team and with our customers. Mission before ego. Everyone contributes. No one coasts. If you’re driven by impact, pace, and raising the bar. This is the place. What You'll Do * Independently manage the full sales cycle from initiation to close, partnering with mid market corporates and law firms to succeed in the age of AI. * Build and progress a strong pipeline through a mix of inbound and outbound efforts, running a tight, repeatable sales process. * Build trusted relationships with key decision makers and stakeholders, uncovering pain points and delivering tailored solutions that drive clear ROI. * Deliver impactful product demonstrations and presentations that move deals forward and drive adoption. * Collaborate cross functionally with Product, Engineering, and Legal to ensure our platform aligns with customer needs and continues to develop at pace. Contribute to refining our mid market sales motion and GTM processes, documenting best practices to help us scale effectively. What You Bring * Have a proven track record of 3 to 6 years of experience in B2B sales, go to market, or a comparable role in a high performing SaaS org, top tier consultancy, or a customer facing role within a relevant industry. * Experience managing end to end deals with multiple stakeholders, navigating procurement or security steps as needed, and consistently hitting targets. * Take clear ownership of quota, outcomes, and customer experience, putting the needs of the business first while maintaining high integrity. * Show perseverance and adaptability, staying focused through ambiguity and learning quickly from what works and what doesn’t. * Are naturally inquisitive and coachable, actively seeking feedback and continuously improving your craft. * Bring strong discovery and storytelling skills, translating complex workflows into simple, value based narratives. * Have enthusiasm for international business development and share our vision of transforming legal work through AI. * Demonstrate a founder like mindset, proactively spotting friction and building scalable systems and playbooks. What’s In It For You * Global collaboration: Partner with teams and clients across Europe, APAC, and North America. * Competitive package: Comprehensive salary, benefits, and tools for success. * Meaningful work: Your efforts shape how thousands of lawyers use AI daily. * In-person environment: Chicago office is designed for ambitious builders. * Benefits & Perks: We invest in our people with a comprehensive, thoughtfully designed benefits package: Medical, Dental & Vision * Multiple medical plan options through Aetna and Kaiser Permanente * HSA or Healthcare FSA (based on plan selection) * Dental plans via MetLife * Vision plans via Vision Care Family Support * Generous parental leave * Free access to Maven Clinic * Dependent Care FSA * Free One Medical membership for employees and dependents Additional Perks * Pre-tax commuter benefits * Life Insurance + STD/LTD * 401(K) with generous company match * Unlimited PTO * Robust voluntary benefits, including identity protection (via Aura), legal coverage via MetLife, pet savings programs, and more Legora is an Equal Opportunity Employer At Legora, we believe great teams are built on diversity of thought and experience. We’re proud to be an equal opportunity employer and committed to creating an inclusive, high-performance culture where everyone can do their best work. We welcome people of all backgrounds and don’t discriminate based on race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, disability, veteran status, or any other characteristic protected by law.

Stripe

WHO WE ARE ABOUT STRIPE Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate net new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. ABOUT THE TEAM The Commercial team is a high-velocity sales team focused on acquiring new, under-penetrated mid-market customers. As an Account Executive on the Commercial Hunter sales team, you’ll be responsible for sourcing and closing net new business, executing outbound sales strategies, and running end-to-end sales cycles to bring new customers onto Stripe. You’ll play a critical role in expanding Stripe’s reach by identifying high-potential prospects and converting them into long-term users of our platform. WHAT YOU’LL DO As a Account Executive, Commercial Hunter you will play an instrumental role in fueling Stripe’s growth by acquiring net new mid-market customers. In this role, you will also help build out a new team and go-to-market (GTM) motion at Stripe. RESPONSIBILITIES * Identify high-potential prospective users and use effective prospecting strategies to generate leads that drive net-new revenue growth in your territory * Develop and implement scaled sales strategies for acquiring new customers and driving adoption of Stripe’s products across new accounts * Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close * Work cross-functionally to solve user pain points and improve our product to better serve new customer needs WHO YOU ARE We’re looking for a high performing, well-rounded seller who can manage high velocity deal cycles, enjoys building and has demonstrated success dealing with ambiguity and operating in a high-growth environment. If you're hungry, persistent and willing to roll up your sleeves to build the plane while we’re flying it, we want to hear from you! MINIMUM REQUIREMENTS * 5+ years full sales cycle/closing experience with net new business accounts * Ability to understand technical requirements and craft solutions across multiple technology products * Ability to perform quantitative analysis and independently manage pricing negotiations  * Strong operational acumen and ability to manage and prioritize a book of 100 accounts  * Ability and motivation to operate in a highly ambiguous and fast-paced environment * Superior verbal and written communication skills * You will be required to work from the Chicago office three (3) days per week PREFERRED QUALIFICATIONS * Prior experience in a sales and/or customer-facing role at a high growth payments company

Trustpilot

At Trustpilot, we're on an incredible journey. We're a profitable, high-growth FTSE-250 company with a big vision: to become the universal symbol of trust. We run the world's largest open customer review platform, and while we've come a long way, there's still so much exciting work to do. Come join us at the heart of trust! At Trustpilot, we’re on a mission to make the world a little more trustworthy by empowering businesses through authentic customer feedback. Our team is a vibrant mix of multinational customer experience specialists who thrive on collaboration, problem-solving, and out-of-the-box thinking. We pride ourselves on being effective listeners and troubleshooters, always ready to tackle challenges together. As a Senior Enterprise Account Executive at Trustpilot, you won’t just be selling a product; you’ll be part of a dynamic Sales team filled with hard-working and motivated professionals who share a passion for delivering exceptional support and value to our diverse customer base. Here, you’ll find that your hard work and dedication are recognized and celebrated. With an empowered and supportive leadership team and peers who inspire each other to excel, you’ll have the tools and resources you need to achieve your targets and grow your career.  We believe that success should be enjoyable, and we make sure that fun is part of the journey. If you’re ready to take on new challenges, make meaningful connections, and be part of a team that is shaping the future of customer experience, then Trustpilot is the place for you! What You’ll Be Doing * Direct the full sales cycle from inception to close, strategically guiding enterprise clients through each stage of the process focusing on high-priority Tier 1 accounts. * Act as a foundational builder for our organization, contributing to the development and refinement of our sales frameworks and operational strategies. * Uncover and capture new vertical opportunities by translating Trustpilot’s value into high-growth greenfield markets. * Conduct outbound sales calls and meetings with C-level executives across various industries, building strong relationships and driving interest with the support of the Enterprise ADR Team’s lead generation efforts. * Drive accurate and ambitious forecasting by maintaining and managing your pipeline efficiently using Salesforce. * Achieve and consistently exceed quarterly sales goals while driving revenue growth for the Enterprise segment. * Collaborate with cross-functional teams to ensure a smooth transition for clients from sales to implementation. Winning together is critical. Who You Are * Extensive inside sales experience in a fast-paced and growing environment, preferably in SaaS or technology sectors. * Embrace a "challenger" mindset, leveraging your deep industry expertise to iterate on our sales processes and drive the evolution of our Enterprise function. * Deeply skilled in comprehensive discovery and navigating complex organizations, with a focus on cultivating trust-based momentum to drive contract value and improve the customer journey. * Proven ability to qualify leads, reach the right contacts, prioritize your pipeline, and successfully close deals. * Strong understanding of the organizational structure within upper mid-size to large enterprises, enabling effective navigation of sales processes. * Ability to thrive in a performance-oriented environment with a focus on achieving efficient sales cycles and driving high initial contract value. * Familiarity with e-commerce, online marketing, and social media trends that can enhance sales strategies and client engagement. What’s in it for you * A competitive base salary ranging from $124,000-$144,000 gross per year plus a competitive commission structure. The base salary range stated doesn't include any variable pay such as bonuses or commission, awards made under Trustpilot's equity program, or other benefits. * A range of flexible working options to dedicate time to what matters to you * 20 vacation days + 2 personal days +10 paid holidays per year * Two (paid) volunteering days a year to spend your time giving back to the causes that matter to you and your community * Rich learning and development opportunities supported through the Trustpilot Academy, LinkedIn Learning and Blinkist * Full health insurance * 401k matching your contributions dollar-for-dollar up to 4% of your base salary * 24/7 Employee Assistance Plan and full access to Headspace, a popular mindfulness app to promote positive mental health * Paid parental leave for employees who have been employed for over 6 months with full full scope of benefit after 12 months * Regular opportunities to connect and get to know your fellow Trusties, including company-wide celebrations and events, ERG activities and team socials * A friendly, fun and open office complete with an onsite gym, gaming room and fully stocked fridge with ever changing snacks and drinks * Communal lunch, extra treats and events in the month -- think ice cream carts, coffee bars and massages, to name a few  Still not sure? We want to be a part of creating a more diverse, equitable, and inclusive world of work for all. We’re excited to hear about your experiences as well as how you will contribute to our working culture. So, even if you don’t feel you don't meet all the requirements, we'd still really like to hear from you! #LI-JL1 About us Trustpilot began in 2007 with a simple yet powerful idea that is more relevant today than ever — to be the universal symbol of trust, bringing consumers and businesses together through reviews. Trustpilot is open, independent, and impartial — we help consumers make the right choices and businesses to build trust, grow and improve. Today, we have more than 350 million reviews and 60 million monthly active users across the globe, with 149 billion annual Trustpilot brand impressions, and the numbers keep growing. We have more than 1000 employees and we’re headquartered in Copenhagen, with operations in  Amsterdam, Denver, Edinburgh, Hamburg, London, Melbourne, Milan and New York.  We’re driven by connection. It’s at the heart of what we do. Our culture keeps things fresh –– it’s built on the relationships we create. We talk, we laugh, we collaborate and we respect each other. We work across borders and cultures to be the universal symbol of trust in an ever-changing world. With vibrant office locations worldwide and over 50 nationalities, we’re proud to be an equal opportunity workplace with diverse perspectives and ideas.  Our purpose to help people and businesses help each other is a tall order, but we keep it real. We’re a great bunch of humans, doing awesome stuff, without fuss or pretense. A successful Trustpilot future is driven by you –– we give you the autonomy to shape a career you can be proud of. If you’re ready to grow, let’s go. Join us at the heart of trust. Trustpilot is committed to creating an inclusive environment where people from all backgrounds can thrive and where different viewpoints and experiences are valued and respected. Trustpilot will consider all applications for employment without regard to race, ethnicity, national origin, religious beliefs, gender identity or expression, sexual orientation, neurodiversity, disability, age, parental or veteran status. Together, we are the heart of trust. Trustpilot is a global company and our data practices are designed to ensure that your personally identifiable information is appropriately protected. Please note that your personal information will be transferred, accessed, and stored globally as necessary for the uses and disclosures stated in our Privacy Policy. If you have a disability and would like to discuss any adjustments you might need either in submitting your application, or to the recruitment process more generally, please let us know by contacting our Talent Acquisition Team (talent.acquisition@trustpilot.com) quoting the role you wish to apply for.