Caity Begg of Authentic Social: “ Always Be Closing!”

People are afraid of rejection, and this is why so many resist sales. Sales is a numbers game — not every deal will work out or be perfect. It is important to be prepared to answer any common objections prospects may have in a calm, even, and helpful manner — answering their objections while redirecting the conversation back to […]

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People are afraid of rejection, and this is why so many resist sales. Sales is a numbers game — not every deal will work out or be perfect. It is important to be prepared to answer any common objections prospects may have in a calm, even, and helpful manner — answering their objections while redirecting the conversation back to specific reasons why your product or service would work for them.


As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Caity Begg.

Caity Begg is the Founder of Authentic Social, focused on helping organizations increase sales through personalized communication + authentic business relationship building at scale. She is a 2016 Harvard graduate and LinkedIn alum. Caity resides in New York City and is also a 2021 Forbes Next 1000 honoree.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

Ever since I was little, I have been passionate about sales and entrepreneurship. I tried it all — lemonade stands, bracelet making businesses, pizza review businesses, and more. In high school, I founded YoungTri, an organization that connected young triathletes worldwide. I completed a half ironman at 14, marathon at 16, and Ironman at 18 (all with my dad) and loved connecting with others who shared these passions across the world. We had members in 30+ countries and every state, and through YoungTri I began to speak across the country about topics related to female empowerment in sports, female involvement in social media, and more. During my senior year in at Harvard, I did my honors thesis on virtual impressions and how digital communication affects the way we interact as well as form and develop relationships. From this, I found that the more we align our personal selves with our digital selves, the higher the ROI both in personal and professional settings. From there, I started Authentic Social. I then worked at LinkedIn for a year after graduation and grew Authentic Social on the side. One year after starting at LinkedIn, I left to pursue Authentic Social full time. I have been full time with Authentic Social since October 2017. At Authentic Social, I focus on social selling and authentic marketing strategy.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

I missed my weeklong sales training at LinkedIn to do a photo shoot with Vineyard Vines in the Virgin Islands. I was in potential trouble at the time, because you weren’t supposed to miss this mandatory training. My manager Tera was extremely accommodating and let me go on the trip, and I promised that I would make her proud by doing well when I came back. Even without training, I ended up being #1 on my team — and everything worked out well. Tera had an incredible impact on my career, and almost five years later I still keep up with her through social media!

Are you working on any exciting new projects now? How do you think that will help people?

I’m working on a large-scale productized version of Authentic Social’s social selling methodology. The first installment of this will be a course targeted towards executives and how they can leverage LinkedIn to generate more leads and improve their personal brand. Further installments will include specific modules on how businesses can sell in a more personalized manner to both increase revenue and maintain lasting, authentic professional relationships. My work right now focuses predominantly in the legal, financial, and business to business sales industries, although the methodologies are also more widely applicable. I am also growing my “Career Convos with Caity” series, a free resource for those looking for jobs or career advice.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My family members (especially my mom, dad, and brother TJ) have all been incredibly supportive when it comes to my career. As it pertains to sales and helping to refine this background, my dad Tom Begg is the absolute best. He is a sales wizard who perfectly balances relationship building, prospecting, and closing the deal without seeming “salesy”. He provides me with regular advice on sales strategy, growing my business, and more. During my junior year of high school, he sat me down on the couch and said, “Caity, you’ve got to join LinkedIn.” He was one of the first 100,000 or so members (there are 750 million-plus members now). During my junior year, he walked me through why LinkedIn was so important, emphasizing the importance of affinity groups (like your college or hobby network). My dad also set a great example for me in the way he maintains his personal and professional relationships. He is always doing things for other people and adding value.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

My company Authentic Social focuses on social selling strategy. We work on a retainer basis with companies in the legal, financial services, and B2B sales fields to help overhaul sales and marketing processes. This involves social selling strategy, personalized outreach at scale, social media, thought leadership, employer branding, and more. I also work with companies in creating personalized seminars for social selling, as well as consult executives on these matters. Social selling is all about making sales more personalized — establishing your own personal brand, growing professional relationships, engaging in personalized outreach, thought leadership, and more.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

I try to always take the time to really listen to my friends and family. If I can sense that they are anxious about something, especially something broader in our world, I make an effort to reach out and show that I am there for them. Amidst such uncertain times, human connection is more important than ever — and the best way to support our loved ones is by showing up (whether that be virtually, in person, sending a card, text, or otherwise).

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Our education system ignores sales because sales is often associated with negative sentiments — like being pressured into buying something. However, sales is involved in myriad aspects of life and is important (in some capacity) in more professional careers than one may think. It certainly should be involved in more curriculum.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

“Salesy” is a term that indicates that one party enters into a relationship with a clear motive — to make a sale. A “salesy” person, in the traditionally regarded sense, will stop at nothing to make said sale, even if it means compromising themselves or others. This is not how sales should be at all! I like to redefine salesy by encouraging social selling. Rather than entering into a single relationship with a clear motive to make a sale, social selling helps cultivate personal and professional relationships with meaning. Social selling encourages you to do what is best and show care for your clients and prospects.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

Authentic Social and my personal and expertise focuses on all seven of these stages, but my “secret sauce” starts with prospecting. As prospecting is the first stage in the sales cycle, if this stage is executed incorrectly it affects all subsequent areas of the deal. Ninety percent of decision makers never answer a cold call. When your company’s sales initiatives focus on training salespeople to cold call to prospect, it misses an opportunity to start the sales process at a higher level. The key that I have mastered is training teams to balance efficiency and speed with personalization. For example, it is far more effective to send 40 highly personalized inMails on LinkedIn than a generic email to 500 people. These personalized messages allow you to directly target the decision maker, which saves a ton of time in the sales process.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

Sales is truly about connecting with and becoming a resource to as many people as you can. Our methodology encompasses a number of different factors into the prospecting process, one of which is affinity networks. I’ll give an example. Rather than being “salesy,” when I reach out to a prospect, I try to make some sort of connection. Sometimes this may be a shared college network or hobby like triathlon (or NYC restaurants). Other times you may have nothing in common with a prospect — but you can read a thought leadership article they may have posted and comment on it or show interest in something else that is on their profile. It’s important to truly show interest and not manufacture it. This approach is meant to be relationship first and make the sales process more authentic.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

People are afraid of rejection, and this is why so many resist sales. Sales is a numbers game — not every deal will work out or be perfect. It is important to be prepared to answer any common objections prospects may have in a calm, even, and helpful manner — answering their objections while redirecting the conversation back to specific reasons why your product or service would work for them.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

ABC — Always Be Closing! This means that closing should always be at top of mind for those in sales. However, this does not mean that salespeople should be annoying or pushy in the close. Keep regular touchpoints, but don’t push it. Make sure you’ve answered all possible questions and emphasized that you are there to answer any final questions. It’s the art of the “softsell pitbull” — stay soft in your selling, but never take your goal of closing out of mind. Stay consistent, clear, and creative with follow up.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

As I just mentioned, follow up should be consistent, clear, and creative. First is consistency — the most important thing! Make sure you have an organized list of current prospects and timeline for follow ups. It’s important to think outside the box — everyone is used to getting follow up emails saying “following up on my last note, blah blah blah”. Sometimes a simple follow up note suffices, but other times sending a valuable industry resource to a prospect is better (like a podcast featuring your service or product). I’ve also seen creative methods like postcards or small gifts work — virtual gift cards for rideshare apps or delivery services can be good.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

It’s important to establish communication norms with prospects and clients. Make sure you know which mediums are preferred for the specific executive and company. For example, I have a few clients who prefer text for an urgent message over email. In general as an overarching rule, I would not cold video call to close!

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I started “Career Convos with Caity” at the beginning of the COVID-19 pandemic to apply my social selling strategies to provide free resources to those looking for a job. I’m continuing to work on this and would love to do this at a larger scale to help people find jobs and understand the process as a whole.

How can our readers follow you online?

Readers can follow me online here:

LinkedIn — linkedin.com/in/caityb

Instagram — Instagram.com/caityb

TikTok — tiktok.com/@caitybegg

Thank you for the interview. We wish you only continued success!

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