How do you get creative when following up with the same prospect over and over?

Been running into some challenges trying to break into colder accounts. How do you typically get creative and vary your follow-up attempts after 5,6, or even 7 follow-up emails/ calls?

3
SalesSweetheart
Good Citizen
1
Director of Sales
Memes & Gifs
ApolloCreed
Good Citizen
0
Account Executive
How do you find that works? 
SalesSweetheart
Good Citizen
0
Director of Sales
I usually get a response! I think the monotony of "Following up to see where we are at" and those get old and they have it coming from so many vendors that it is easy to ignore but once I sent the meme from Breakfast Club "Dont forget about me" and with it a short line just asking if it was still being evaluated. I think the personality & humor of it made them feel more relaxed and not pressured and it got a response and steps forward. On numerous occasions I have done this after a few unanswered follow ups and a pretty high percentage get responded to. 
CadenceCombat
Tycoon
1
Account Executive
I find most prospects to be pretty different from one another on some level so most of the repetition is up front and from there, in terms of enterprise software, a one-size-fits-all approach generally doesn’t do the trick which then allows you to showcase some creativity.
LoneMaverick
Executive
0
Strategic Account Leader
It takes a little effort but I’ll look at industry news (typically on hacker news or Medium) to try to share something relevant.  I look at our up coming marketing activities see if there is anything relevant to what we’ve discussed in the past.  I also don’t follow up on the same thread, I create a new email.  
ApolloCreed
Good Citizen
0
Account Executive
Love that, do you find yourself bookmarking relevant posts and just passing that forward once outreach feels stale, or just staying up to date and making those news outlets part of your day?
SaaSCloser
Member
0
Account Executive
Create a personalized video on Vidyard (no, I don't work for Vidyard). Seems to work well.
Sandbagged
0
Account Executive
Agreed. Some of the best responses I've gotten is using personalized video on Vidyard (and no, I don't work for them either) 
CuriousFox
WR Officer
0
🦊
Value makes you stand out.
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