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City Representative - Chicago, IL

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Fast Facts

Join Togetherhood as a City Representative in Chicago, where you'll lead the charge in establishing our presence in the local market by fostering relationships with schools and community centers, and ensuring excellent service delivery to clients.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Responsibilities: Seek new business opportunities in K-12 education, manage existing client relationships, conduct outbound prospecting through various channels, and maintain strong partnerships with local educational institutions.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Skills: Proven sales experience in B2B, effective communication, cold calling, CRM proficiency, and the ability to independently drive account initiatives.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Qualifications: 2+ years in sales, experience in cold outreach, strong planning skills, and a willingness to engage directly with educational environments is preferred.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Location: Chicago, IL, with some required monthly travel to NYC for team meetings.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Compensation: Not provided by employer. Typical compensation ranges for this position are between $50,000 - $70,000.



About Togetherhood

Togetherhood is revolutionizing enrichment and education for children from preschool to high school. We are a fast-growing technology marketplace that makes it super simple for communities to create world class enrichment programs. We serve schools, community centers, residential communities and homeschooling communities. Our mission is to provide all communities with access to high quality enrichment and education. The company was founded by a repeat entrepreneur with a strong track record of success (two acquisitions, one IPO as Chief Product Officer at Farfetch).

What you’ll do

Togetherhood is growing and we are seeking a City Representative to help us launch the Chicago market! Because you will be Togetherhood's sole employee representative in the Chicago market, your responsibilities will be different from those of a typical City Representative. Not only will you focus on new business and lead generation, you will also be responsible for managing and growing the Chicago portfolio. In addition to cold calls, drop ins, email marketing and other sales techniques, you will also be visiting current clients and making sure that their needs are being met and Togetherhood is exceeding their expectations. You will use your knowledge of Chicago to target Chicago’s top schools and suburbs.

If you love both pre- and post-sale activities, this is a great opportunity for you to get meaningful experience with both job functions. This role is narrowly focused on candidates who live in the greater Chicago area - expectations are a blend of remote work, field work to prospective local clients and monthly visits to Togetherhood HQ in NYC. Please only apply if you are (1) living within a close proximity to Chicago (2) are able to do local field visits on a daily basis and (3) willing to come to NYC on a monthly basis to meet with the NYC team.

Primary responsibilities will include seeking new business opportunities by contacting and developing relationships with potential customers in the preschool and K-12 education space, as well as managing mid-late stage deals and active client relationships.

A day in the life of a City Representative:

  • Creatively research targeted accounts to identify key contacts and critical account information prior to prospecting
  • Work collaboratively with our NYC Sales and AM team to align on outreach strategy
  • Execute outbound prospecting through a multi-channel approach: cold calls, email sequences, LinkedIn, client gifting, hand-written notes, and more (bring ideas)
  • Be a subject matter expert on the Togetherhood suite of services/products and how we solve high priority problems for our clients (preschool and K-12) as well as differentiating us from competitors
  • Bringing qualified leads to close
  • Driving partner performance by managing day to day issues as they arise, advocating for the partner’s best interests and collaborating with the client to provide a dynamic enrichment program
  • Influencing partners to deepen their partnership with Togetherhood via seasonal renewal cycles and QBRs
  • Visiting partner sites on a recurring cadence, along with other communication touchpoints, to understand gaps and maintain a strong relationship

Tools include Hubspot, Notion, Quickbooks and other software that increases the productivity of our team.

This is a great opportunity to join a mission driven organization that helps children across the Tristate area access high quality enrichment and enables teaching artists and coaches to get paid what they deserve. As well, you will be working in a high-growth environment with potential for advancement and job development.

Who you are

Your experience:

  • Proven sales experience with ideally 2+ years experience prospecting and/or closing B2B prospects
  • Door-to-door sales experience (or any environment where you faced considerable rejections) is a plus
  • Experience using CRM Software like HubSpot or similar
  • Comfort with cold call activities to prospects
  • Track record of meeting and exceeding targets or professional goals
  • Demonstrable ability to prospect and tenacity to find the decision makers within an organization
  • You are able to own account-related initiatives and drive them to completion, with an ability to navigate ambiguity and build scalable processes.

Your proficiencies:

  • Effective communications skills (verbal, written, and listening)
  • Strategic and detail-oriented planner with strong ability to identify and follow-through on leads to create new sales qualified opportunities
  • Ability to work independently with high productivity with an early stage startup
  • Willing and enthusiastic about pitching in when necessary, including standing in as a one-off sub if we are unable to secure a sub for a class. (This almost never happens, but it can happen on occasion in a new market when our instructor network is nascent. You'd need to be comfortable leading a class with a lesson plan that we’d supply.)

Your Superpowers

  • Curiosity! You love asking questions and follow up questions! But retain what you learn.
  • Extraordinarily out-going. You embrace meeting new people and are able to create real, fruitful relationships with a wide array of individuals.
  • Entrepreneurial. You’re willing and excited to work within a high growth company with limited formal structure. You’re eager to test new things and seek continual improvement. You are a self-starter!
  • Someone who embraces failure. Getting turned down by a potential client doesn’t bring you down. It makes you focused on how to rework the solution for future conversations.
  • An on-the-fly problem solver. We are brainstorming to build an exceptional system within each client. It’s our job to WOW our clients, and it all starts with you as you’re often the first impression clients will have of Togetherhood.
  • Extremely hard working. We are a startup with the mentality that no job is too big or too small for us. You hustle because that’s just how you work.
  • Calm and collected in the line of fire. On a day where everything that could go wrong has gone wrong, you find a way to stay positive.
  • Passionate about growth. We have a bright future ahead, which depends on our team’s spirit, morale, and work ethic.
  • Exceptionally good listener. You read people well. Your EQ is off the charts, and you have a unique, even uncanny ability to pick up on people's needs without them even saying it.
  • Highly attentive to detail. You proofread every correspondence several times, and then another before it goes out. Your work is accurate, error-free, concise and conveys a deep understanding of the intricacies of our partner relationships.
  • Able to secure relevant clearances to work with children in the state of Illinois. In the event that you need to be in a classroom setting with students, customer accounts need to know you are cleared to do so.
  • Comfortable communicating not only with directors at customer accounts, but also students and parents at customer accounts.

Average salary estimate

$60000 / YEARLY (est.)
min
max
$50000K
$70000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About City Representative - Chicago, IL, Togetherhood

Are you ready to take the lead as a City Representative with Togetherhood in Chicago, IL? This is an exciting opportunity for someone with a passion for education and community! In this role, you'll be at the forefront of establishing Togetherhood's presence in the Chicago market, building strong relationships with local schools and community centers. You'll be responsible for seeking new business opportunities in K-12 education while managing existing client relationships, ensuring they receive exceptional service. With your proven sales experience, you’ll conduct outreach through cold calling, email campaigns, and personal visits to schools, all in an effort to provide top-notch enrichment programs. Not only will you be driving business growth, but you’ll also be an advocate for our clients, making sure their needs are met and expectations exceeded. If you're someone who thrives in a dynamic environment and enjoys both pre-sale and post-sale activities, this position has your name written all over it! You'll join a team that values your input as Togetherhood continues to grow, and you'll get access to cutting-edge tools to help you succeed. If you live in the greater Chicago area and are ready to bring your entrepreneurial spirit, effective communication skills, and passion for education to our mission, we want to hear from you!

Frequently Asked Questions (FAQs) for City Representative - Chicago, IL Role at Togetherhood
What are the main responsibilities of a City Representative at Togetherhood in Chicago?

As a City Representative at Togetherhood in Chicago, your main responsibilities include seeking new business opportunities in the K-12 education sector, managing client relationships, and conducting outbound prospecting through various channels. You'll actively engage with local educational institutions to foster and maintain partnerships, ensuring exceptional service delivery. This role is multifaceted and allows you to engage in both pre-sale and post-sale activities.

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What qualifications do I need to become a City Representative in Chicago with Togetherhood?

To qualify for the City Representative position with Togetherhood in Chicago, you should have at least 2 years of sales experience, preferably in a B2B environment. Experience with cold outreach is essential, and familiarity with CRM software like HubSpot is a plus. We also appreciate strong planning skills and the willingness to engage directly with schools and community centers in the area.

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How does the City Representative role at Togetherhood differ from traditional sales positions?

The City Representative role at Togetherhood is unique as it combines responsibilities of business development with account management. Unlike typical sales positions that focus solely on lead generation, this role also involves maintaining strong relationships with existing clients and ensuring their needs are met. You will have a blend of remote work and field visits, which adds variety to your day-to-day activities.

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What skills are essential for the City Representative position with Togetherhood?

Essential skills for the City Representative position with Togetherhood include effective communication, the ability to conduct cold calls, and proficiency in CRM software. You should also possess strong planning abilities, be independent in driving account initiatives, and have a knack for building relationships with diverse individuals across educational settings.

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What is the work environment like for a City Representative at Togetherhood in Chicago?

The work environment for a City Representative at Togetherhood is fast-paced and dynamic. You will be working both remotely and on-site with clients, which offers a mix of independent work and collaborative opportunities with the NYC team. The culture is rooted in creativity, collaboration, and a strong mission to improve educational experiences for children in communities.

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Common Interview Questions for City Representative - Chicago, IL
Can you describe your previous experience in B2B sales?

When answering this question, highlight specific roles where you demonstrated success in sales, focusing on metrics or achievements that showcase your ability to meet or exceed targets. Mention your experience in cold outreach and managing customer relationships, emphasizing any relevant industry knowledge related to education.

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How do you handle rejection in a sales role?

It's important to acknowledge that rejection is part of the sales process. Share a personal experience where you faced rejection but learned from it. Discuss how you adapted your strategy or messaging based on feedback, showcasing resilience and a focus on continual improvement.

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What strategies do you use for prospecting new clients?

Discuss various prospecting strategies you've employed, like leveraging social media, cold emailing, or attending networking events. You could mention how you research and identify potential leads, ensuring your approach is targeted and personalized to each client.

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How do you maintain relationships with existing clients?

Explain your approach to relationship management, focusing on consistent communication, understanding their needs, and proactively addressing any issues that arise. Share examples of how you have helped clients optimize their experiences, ultimately leading to a long-term partnership.

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Describe a successful sales pitch you made.

When sharing a sales pitch, outline the situation, the preparation that went into the pitch, and the outcome. Focus on what made your pitch successful, whether it was your understanding of the client’s needs, how you articulated the value of your solution, or the follow-up processes you engaged in.

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What CRM tools have you used, and how did they help you?

Be prepared to discuss your familiarity with specific CRM tools, such as HubSpot. Explain how these tools have helped you streamline your sales processes, track leads, and manage client interactions, showcasing how they contributed to your success in previous roles.

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How do you prioritize your sales activities?

Share your approach to time management and prioritization, explaining how you assess leads based on potential value. Discuss methods like setting daily or weekly goals, analyzing account potential, and focusing on high-impact activities that drive revenue.

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How do you stay informed about industry trends and competitor activity?

Explain your strategies for staying updated, whether through reading industry publications, participating in networking events, or engaging with peers in the field. Highlight your willingness to continuously learn to maintain a competitive edge.

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What do you believe sets Togetherhood apart from its competitors?

Research Togetherhood’s mission and values to articulate why you believe it stands out. Consider touching on the focus on community building, the unique offerings in educational enrichment, and the company culture, showing that you are aligned with their goals and values.

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What motivates you to succeed in a sales environment?

Share personal motivations, whether they be achieving personal goals, the thrill of closing deals, or a passion for making an impact within the educational space. Connect your motivations to the mission of Togetherhood to show alignment.

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EMPLOYMENT TYPE
Full-time, hybrid
DATE POSTED
April 9, 2025

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