Sales Development Rep (and/or first Sales hire at VC-backed startup 🚀🚀🚀)

Offsite Remote

Why Offsite?

While there are many benefits for employers and employees alike in working remotely, running any company is challenging enough, let alone a remote-first organization.

Offsite ( is helping create more engaged, connected, and empathetic workplaces of the future by allowing People Leaders at high-growth tech companies to easily plan, manage, and follow-up after team retreats and other types of Offsites.

Offsite is looking for our first Sales Development Rep (or first Sales hire, if you're overqualified for an SDR role but still interested), to work hand-in-hand with our co-founders, and to be up-skilled and promoted within 12 months, and path to further potential career development from there.

This is a unique opportunity to:

👉 join a VC-backed startup as one of our first full-time employees...

👉 work wherever you want, however you want (so long as you have exceptional WiFi connection), with invitation to quarterly team retreats and other fun Offsites we're planning for our team and our clients

👉 build a network of CEOs, Chiefs of Staffs, EAs, and People Leaders from the world's fastest-growing and most inspiring companies...

👉 have day-to-day impact on the direction of our company through helping us hit aggressive growth goals that will boost our ability to raise future rounds of funding...

👉 gain intentional investment into your education, with membership into communities like RevGenius and regular calls with select investors/advisors of Offsite who have vast sales experience to prep you for your promotion...

👉 and so much more!

About Offsite:

Offsite ( provides our clients (ie high-growth companies) with stress-free, end-to-end team retreat, client-facing, and other "offsite" planning.

We also provide our partners (ie hotels, meeting spaces, and other types of vendors) with new sources of revenue while saving them time on marketing and fulfillment of their services.

Our clients include YC-backed, Inc 5000, and venture-funded companies, as well as soon-to-IPO tech unicorns, global consulting firms, and venture capital firms.

Our team is a "Meeting of the Minds" encompassing serial entrepreneurs with something to prove, who also lead well-rounded lives and care deeply about our work.

  • Jared Kleinert, Co-Founder/CEO - first 10 employees at 15Five turned serial entrepreneur, TED & TEDx speaker, 3x award-winning author, and angel investor. Jared has been named USA Today's "Most Connected Millennial" and has planned or facilitated dozens of Offsites before starting this company.
  • Keir Weimer, Co-Founder/COO - serial entrepreneur behind multiple 7-figure businesses in real estate & hospitality (as the founder of fast-growing luxury hotel brand Weekender), multimedia, and investment. Keir intimately understands the wants and needs of our vendors, namely fellow hotel owners/operators, who we are relying on to provide our clients with the backdrops to host transformational Offsites.
  • Lindsey Lerner, Head of Client Success - self-described "Human Swiss Army Knife" who has started companies in travel, co-working, photography, and consulting. Lindsey is a recent OnDeck graduate and is our main point of contact with beta clients.
  • Andrew Scales, Full Stack Engineer - Andrew joined us from The Wanderlust Group, a Series B-backed marketplaces startup with assets including Dockwa and He is also a former startup founder, 2-time national champion in whitewater rafting, and creator of the CheesySnacks NFT collection on OpenSeas.
  • Jenny Grace, Marketplace Development -** former US Brand Marketing & Experiences Manager for Mr & Mrs Smith, one of the leading clubs with over 1M members searching their vetted marketplaces for boutique hotels and travel inspiration. Jenny was also a casting associate in Hollywood, worked as an Associate Producer at a boutique music production studio, and taught english in the small, West African country of Togo for 5 months.

We're backed by diverse angel investors like:

  • Ryan Simonetti (Co-Founder/CEO of Convene),
  • Michael Lisovetsky (Partner at Magic Fund and Co-Founder of JUICE, which is the #105 fastest-growing private company in the US according to Inc 5000),
  • Stacey Ferreira (Co-Founder of Forge and MySocialCloud, both acquired. Thiel Fellow and Forbes 30 Under 30 honoree, now Director of New Formats at GameStop),
  • Abhi Goel (serial tech entrepreneur; Co-Founder/CTO of cloud infrastructure-as-a-service company which was acquired in 2017),
  • Marshall Mosher (founder of Vestigo; Global Impact Challenge winner at Singularity University),
  • Alan Quigley (associate at Aflac Global Ventures),
  • Henry Lee (co-founder/COO of HD Made, a digital design and strategy agency with clients including NASDAQ, Robin Hood, FanDuel and NYCEDC),
  • Keyaan Williams (global cybersecurity expert and Founder of CLASS-LLC),
  • Calvin Correli - (Founder of,
  • David Nassau - (Senior Product Marketing Manager at Intel),
  • Declan Baldwin (Oscar-winning film producer and founder of Big Indie Pictures), and others.

We also recently completed an accelerator program with Forum Ventures (formerly known as Acceleprise) and will participate in a Demo Day with Forum in April 2022, which is when we will raise our Seed Round.

We are building a company to serve the needs of our clients and partners for decades to come, as the future of work continues to take shape, and with this hire we are looking to find a founding team member who is excited by the promise of #startuplife.

About The Role

This is a rare opportunity to be paid to learn.

Not only that, but you get to chart your own path in a high-growth, VC-backed startup that is defining an industry, and contribute meaningfully to all aspects of company growth.

After being at Offsite for 2-4 years, you will be ready to lead a sales team of your own! Hopefully, you'll be leading our sales team en route to a successful IPO or 9+ figure exit 🚀.


This is not necessarily an entry-level SDR role, nor will this entail only traditional SDR duties and responsibilities. Within first 1-2 months, you will be on sales calls with qualified prospects selling directly alongside sales team, and developing skills to grow into an Account Executive.

We want you to quickly grow into a leader at our company, and become an Account Executive within our fast-growing organization after evaluating performance in this specific role after a full year with us (potentially sooner based on performance and growth), as we continue building a fast-moving, remote-first company.

Being a Sales Development Rep at Offsite will look like the following:


As our 1st Sales Development Representative (and first employee in our sales department full stop!) you will be joining Offsite at the ground level and will work directly with the cofounders to build the sales department.

You will have direct input, impact and contribution in the early stages of architecting the revenue strategy, framework and systems needed to build and then scale a high-growth service-to-SaaS product apparatus.

You will be responsible for both inbound prospecting and sales work as well as building outbound strategy and executing against it. Work will include filtering and nurturing leads at the initial stages in the sales funnel and successfully booking sales calls for yourself and cofounders to take at this stage, then handing off to Account Executive in coming months.

You will also be building a sales database, researching potential clients, connecting with key ideal client avatar prospects, sending educational materials, answering questions, and qualifying prospects before passing them on to the Account Executive team. 

You will be responsible for researching, prospecting and adding to CRM target ideal clients, identifying their needs, introducing Offsite and our service and value-add product that solves their problem, and generating a pipeline of prospects and accounts.

If you are a self-starter, hungry to learn, would like to work directly with experienced founders and the executive team at an early-stage, VC-backed startup, and are not scared of a challenge and all the reward that comes with that, then this position and company could be a great fit!

What You'll Be Doing

Focus Area


  • Research prospect contact information from identified data sources, lists, and resources and curate creative techniques to get in touch with them
  • Segment market, source data, build database and lists, filter and prioritize outreach
  • Nurture and qualify leads from various channels including MQLs and outreach efforts
  • Prospect into warm and cold accounts and actively manage all sales and prospect activity in CRM

Focus Area

Cold Calls/Email Sequences

  • Drive Offsite revenue and growth through systematic communication strategy developed with founders and exec team to include emails, phone-calls, LinkedIn messages and other channels to reach prospects with a focus on setting sales call appointments

Focus Area

Data And Sales Quota Management

  • Hold yourself accountable for meeting and exceeding quotas by being a master at understanding Offsite and the service and product offering, and knowing how to sell it successfully
  • Work closely with Sales & Marketing on various projects in support of sales goals of organization
  • Be determined and diligent: Conduct high volume outbound call and email campaigns into target accounts until meetings are set and opportunities are created
  • Hit and/or exceed weekly quota to ensure revenue objectives are met
  • Learn through informational sessions and self-teaching to learn the ins and outs of software tools like Hubspot,, Zoom Info,, and LinkedIn Sales Navigator, etc.

Focus Area

Lead Qualification

  • Educate prospects continually on the value of Offsites, the talking points we will train you on, and the ROI for hosting these, and why hosting them without a trusted partner like Offsite costs more and produces less

What You'll Need

  • Bachelor's degree or relevant sales experience (at least 2 years)
  • Entrepreneurial thinking and background preferred and a plus
  • Experience in selling software solutions is a HUGE plus
  • Experience with managing Hubspot CRM and other software platforms, or demonstrated ability to learn new tech quickly
  • Strong written and verbal communication skills
  • You are highly motivated, a self-starter, confident but yet always a student of your craft and the world
  • Excited to be a part of an early-stage, VC-Backed, high-growth technology startup and the opportunity to learn new skills and hyper-charge your career development
  • Ability to grow in a fast-paced, high-growth, always-evolving startup environment
  • Demonstrated coachability, humility, and motivation

Who You Are

  • Strong communicator in all forms (written, verbal, non-verbal, etc.)
  • Desire and ability to build longterm relationships with prospects
  • Passionate about seeking and reaching your full potential personally and professionally
  • Demonstrated accountability and responsibility in all endeavors
  • Effectively articulate ideas, thoughts, solutions and strategies to problems encountered
  • Growth mindset a must in all affairs, open to coaching and mentorship
  • Open to vulnerability
  • Committed to lifelong learning, and growth
  • Self-motivated, self-starter, self-accountable

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